3-Amino-1-propanol → N-((1R)-1-(3-hydroxypropylcarbamoyl)-2-phenylethyl)-N-methylcarbamic acid tert-butylester

3-Aminopropan-1-ol (0.39 mL, 5.12 mmol) was added at room temperature to a solution of N-tert-butoxycarbonyl-N-methyl-D-phenylalanine (1.30 g, 4.65 mmol) in N,N-dimethylformamide (40 mL). 1-Hydroxybenzotriazole monohydrate (0.63 g, 4.65 mmol) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (0.89 g, 4.65 mmol) were added successively. The reaction mixture was stirred for 22 h at room temperature. It was diluted with 10% sodium hydrogensulfate solution (300 mL) and extracted with ethyl acetate (4×100 mL). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo and the crude product was purified by flash chromatography on silica (45 g) with dichloromethane/methanol (10:1) to give 1.01 g of N-((1R)-1-(3-hydroxypropylcarbamoyl)-2-phenylethyl)-N-methylcarbamic acid tert-butylester.

1. extractionextracted with ethyl acetate (4×100 mL)
2. dry with materialThe combined organic layers were dried over magnesium sulfate
3. customThe solvent was removed in vacuo
4. customthe crude product was purified by flash chromatography on silica (45 g) with dichloromethane/methanol (10:1)

ORD 기록

ord-ca29408981794951a12748b33cccb0e9

출처 데이터셋

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06127391