Water → 3-[[(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester

HRID 742386노트

반응식

HRID 742386 반응식
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.CCN=C=NCCCN(C)C.Cl.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:44]([O:51][C:52](=[O:56])[CH2:53][CH2:54][NH2:55])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C(N(C(C)C)CC)(C)C>ClCCl>[C:1]([NH:8][C@H:9]([C:17]([NH:55][CH2:54][CH2:53][C:52]([O:51][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:56])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

참가 물질

7

반응물 5

HCID 962WaterHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 135021004-Methylbenzene-1-sulfonic acid--benzyl beta-alaninate (1/1)

생성물 1

HCID 136862023-[[(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Boc-L-phenylalanine (1.32 g, 5.00 mmol) was dissolved in dichloromethane (50 mL) and treated with HoBt.H2O (1.53 g, 2.00 mmol) followed by WSCDI (water soluble carbodiimide) (1.00 g, 5.24 mmol). After stirring for 40 minutes, β-alanine benzyl ester tosylate (1.85 g, 5.27 mmol) was added, followed by DIPEA (diisopropylethylamine) (1.29 g, 10 mmol). Stirring was continued overnight, then the solvent removed. The residue was dissolved in ethyl acetate (30 mL) and washed with water, 10% sodium bicarbonate solution, then 10% citric acid solution. The organic layer was dried (MgSO4) and evaporated to a white solid--a single component by TLC, 1.74 g, 82% of (32). NMR (CDCl3) δ 1.41 (9H, s), 2.47 (2H, m), 3.01 (2H, m), 3.45 (2H, m), 4.25 (1H, br.q), 5.00 (1H, br.s), 5.07 (2H, s), 6.21 (1H, br.t), 7.15-7.38 (10H, m).

후처리

  1. additiontreated with HoBt
  2. stirringStirring
  3. waitwas continued overnight
  4. customthe solvent removed
  5. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  6. washwashed with water, 10% sodium bicarbonate solution
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customevaporated to a white solid

출처 및 근거

ORD 기록
ord-6059e3bfc6364ca9b7a0e41cc0b4ab9b
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05554643

반응 노트

불러오는 중…