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 852574ノート

反応式

HRID 852574 の反応式
[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

参加物

6

反応物 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

生成物 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 ester収率 48%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1d2d8f6aacb7402e83b76fcba3c7e590
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

反応ノート

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