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

HRID 495819노트

반응식

HRID 495819 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6]([O:10][C:11]([N:13]([CH3:25])[C@@H:14]([C:22](O)=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OC(=O)N(C)[C@@H](C(=O)N(C)[C@@H](C(=O)NCC1CCCO1)CC1C=CC=CC=1)CC1C2C(=CC=CC=2)C=CC=1)(C)(C)C.S([O-])(O)(=O)=O.[Na+]>[C:6]([O:10][C:11](=[O:12])[N:13]([C@@H:14]([C:22](=[O:23])[NH:1][CH2:2][CH2:3][CH2:4][OH:5])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:25])([CH3:7])([CH3:9])[CH3:8]

참가 물질

8

반응물 4

HCID 90863-Amino-1-propanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7015127N-Boc-N-methyl-D-phenylalanine

생성물 1

HCID 54054214N-((1R)-1-(3-hydroxypropylcarbamoyl)-2-phenylethyl)-N-methylcarbamic acid tert-butylester수율 64.6%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 516919Sodium Bisulfate용매HCID 10555137Methyl-((1R)-1-(methyl-((1R)-2-phenyl-1-(((tetrahydrofuran-2-yl)methyl)carbamoyl)ethyl)carbamoyl)-2-(1 naphthyl)ethyl)carbamic acid tert butylester용매

실험 절차

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 1 0% 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)-2phenylethyl)-N-methylcarbamic acid tert-butylester.

후처리

  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)

출처 및 근거

ORD 기록
ord-ed1701f633cf48e78e73a1ca576b2b57
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939880B2

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