(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 446993ノート

反応式

HRID 446993 の反応式
[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]

参加物

4

反応物 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

生成物 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 ester収率 98.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 21584119Ethylacetate methanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-44e4170b77fb4fd4af53621f3d72224d
出典データセット
uspto-grants-2013_07
特許番号
US08481495B2

反応ノート

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