1-Hydroxybenzotriazole → [(2R,3S)-2-Hydroxy-3-({1-[3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-phenyl]-methanoyl}-amino)-4-phenyl-butyl]-carbamic acid benzyl ester

HRID 852574노트

반응식

HRID 852574 반응식
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:15]=1)[C:10]([OH:12])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH2:45]([O:52][C:53](=[O:67])[NH:54][CH2:55][C@@H:56]([OH:66])[C@@H:57]([NH2:65])[CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(Cl)Cl>[CH2:45]([O:52][C:53](=[O:67])[NH:54][CH2:55][C@@H:56]([OH:66])[C@@H:57]([NH:65][C:10]([C:9]1[CH:13]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:15]=[C:7]([N:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[O:1])[CH:8]=1)=[O:12])[CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 693571053-(2-Oxo-pyrrolidin-1-yl)-5-pentyloxy-benzoic acidHCID 69358558phenylmethyl [(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]carbamate hydrochloride

생성물 1

HCID 69359603[(2R,3S)-2-Hydroxy-3-({1-[3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-phenyl]-methanoyl}-amino)-4-phenyl-butyl]-carbamic acid benzyl ester수율 48%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of 3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzoic acid (A13) (530 mg, 1.82 mmol, 1 equiv) in CH2Cl2 (20 ml) were added HOBT (300 mg, 2.2 mmol, 1.2 equiv) and EDAC.HCl (420 mg, 2.2 mmol, 1.2 equiv). After stirring for 5 min, 3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzoic acid hydrochloride (D104) (570 mg, 1.82 mmol, 1 equiv) was added and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was then diluted with CH2Cl2 (20 ml) washed with saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo to give [(2R,3S)-2-hydroxy-3-({1-[3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-phenyl]-methanoyl}-amino)-4-phenyl-butyl]-carbamic acid benzyl ester (D105) (510 mg, 48%) as a white solid.

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 16 h
  2. washwashed with saturated aqueous NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1d2d8f6aacb7402e83b76fcba3c7e590
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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