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CAS RN: 71432-55-8 | 產品號碼: B4178
O-tert-Butyl-N,N'-diisopropylisourea
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產品規格
| Appearance | Colorless to Almost colorless clear liquid |
| Purity(Nonaqueous Titration) | min. 98.0 % |
性質
| 沸點 | 61 °C/10 mmHg |
| flp | 135 °C |
| 比重 | 0.84 |
| 折射率 | 1.43 |
GHS
相關法規
運輸資料
| HS編碼* | 2925.29-000 |
Application
TCI Practical Example: Reagent for tert-Butyl Esterification
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Used Chemicals
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- Boc-Ser-OH [B1637]
- O-tert-Butyl-N,N'-diisopropylisourea [B4178]
- Dichloromethane
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Procedure
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To a solution of Boc-Ser-OH (0.94 g, 4.6 mmol) in dichloromethane (10 mL) O-tert-Butyl-N,N'-diisopropylisourea (3.3 mL, 14.0 mmol) was added dropwise over 5 min at 3 °C then stirred overnight at room temperature under nitrogen atmosphere. To the reaction mixture hexane (10 mL) was added then filtered through celite and the solvent was removed under reduced pressure. The residue was purified by column chromatography (1:1 ethyl acetate / hexane on SiO2), giving Boc-Ser-OtBu as a white solid (0.59 g, 50% yield).
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Experimenter's Comments
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The reaction mixture was monitored by TLC (hexane : ethyl acetate = 1:1, Rf = 0.60).
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Analytical Data（Boc-Ser-OtBu）
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1H NMR (400 MHz, CDCl3); δ 5.57–5.30 (m, 1H), 4.36–4.15 (m, 1H), 3.97–3.79 (m, 2H), 2.57–2.34 (m, 1H), 1.51-1.41 (m, 18H).
13C NMR (101 MHz, CDCl3); δ 169.9 (2 C), 82.8, 80.3, 64.3, 56.5, 28.4 (3 C), 28.1 (3 C).
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Lead Reference
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- L-Type amino acid transporter 1 activity of 1,2,3-triazolyl analogs of L-histidine and L-tryptophan
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Other References
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- Esterification and Alkylation Reactions Employing Isoureas
Application
tert-Butyl Esterification Reagent
Typical Procedure:
The starting material (310 mg, 0.87 mmol) in CH2Cl2 (15 mL) is allowed to react with O-tert-butyl-N,N’-diisopropylisourea (2 mL, excess) and the mixture is stirred under reflux for 12 h. Rotary evaporation and chromatography (hexane : Et2O = 1 : 1) gives the desired tert-butyl ester (260 mg, 0.63 mmol, Y. 72%) as a colorless oil.
The starting material (310 mg, 0.87 mmol) in CH2Cl2 (15 mL) is allowed to react with O-tert-butyl-N,N’-diisopropylisourea (2 mL, excess) and the mixture is stirred under reflux for 12 h. Rotary evaporation and chromatography (hexane : Et2O = 1 : 1) gives the desired tert-butyl ester (260 mg, 0.63 mmol, Y. 72%) as a colorless oil.
References
- Total synthesis of citrafungin A
考研文獻
TCIMail
[TCIMAIL No.168] Alkylation Reagents for Ester Synthesis[TCI Practical Example] tert-Butyl Esterification Utilizing the Isourea Derivative
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