Sodium Hydroxide → 4-(2-Phenyl-cyclopropylcarbamoyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

HRID 31378

반응식

HRID 31378 반응식
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([C:10](=[O:21])[NH:11][CH:12]2[CH2:14][CH:13]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:7][N:6]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=[O:4].[OH-].[Na+]>C1COCC1>[CH2:25]([O:24][C:22]([N:6]1[CH2:7][CH:8]([C:10](=[O:21])[NH:11][CH:12]2[CH2:14][CH:13]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])=[O:23])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 691973874-(2-Phenyl-cyclopropylcarbamoyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

생성물 1

HCID 691978094-(2-Phenyl-cyclopropylcarbamoyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-(2-Phenyl-cyclopropylcarbamoyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (422 mg, 1 mmol) in THF (2 mL) was added 1 N NaOH (1.5 mL) at 0° C. with stirring. After 30 min at 0° C. and 16 h at room temperature, the reaction mixture was concentrated and treated with EtOAc and 6 N HCl (5 mL). The organic layer was dried over MgSO4 and concentrated. The residue was purified by a silica gel column using CH2Cl2/MeOH (95:5) as eluant to yield the desired compound as a colorless oil (343 mg, 84%).

후처리

  1. concentration16 h at room temperature, the reaction mixture was concentrated
  2. additiontreated with EtOAc and 6 N HCl (5 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by a silica gel column

출처 및 근거

ORD 기록
ord-91dcda0975404d5b8b9d406eb83b22ee
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425633B2

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