(1-{1-[4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester → (1-{1-[4-(2-Amino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester

HRID 446993노트

반응식

HRID 446993 반응식
[C:1]([O:5][C:6](=[O:56])[N:7]([CH:9]([C:11](=[O:55])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[N:25]([C:41](=[O:54])[CH2:42][NH:43]C(OCC3C=CC=CC=3)=O)[CH2:26][CH:27]([C:28](=[O:40])[NH:29][C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO.CCOC(C)=O>[C:1]([O:5][C:6](=[O:56])[N:7]([CH:9]([C:11](=[O:55])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[N:25]([C:41](=[O:54])[CH2:42][NH2:43])[CH2:26][CH:27]([C:28](=[O:40])[NH:29][C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:15])([CH3:17])[CH3:16])[CH3:10])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

참가 물질

4

반응물 1

HCID 67280489(1-{1-[4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester

생성물 1

HCID 67280817(1-{1-[4-(2-Amino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester수율 98.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 21584119Ethylacetate methanol용매

실험 절차

A solution of 59 (430 mg, 0.56 mmol) in 1:1 MeOH/EtOAc (4 mL) was treated with Pd/C (5% wet, ca. 100 mg) and placed under H2 (35 psi) using a Parr apparatus. After 3 h, the reaction mixture was filtered through syringe filter disc (Acrodisc-PSF-0.45 μM) and rinsed with MeOH. The filtrate was concentrated to afford crude 60 (350 mg) which was concentrated twice from anhydrous toluene (50 mL) and then used without further purification. Mass spectrum, m/z [637.5] (M+H)+.

후처리

  1. filtrationthe reaction mixture was filtered through syringe
  2. filtrationfilter disc (Acrodisc-PSF-0.45 μM)
  3. washrinsed with MeOH
  4. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-44e4170b77fb4fd4af53621f3d72224d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481495B2

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