4-(2-Benzyloxycarbonylamino-3,3-dimethyl-butyryl)-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester → 4-(2-Amino-3,3-dimethyl-butyryl)-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

HRID 1965189ノート

反応式

HRID 1965189 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:10]2[N:22]([C:25](=[O:42])[CH:26]([NH:31]C(OCC3C=CC=CC=3)=O)[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:24][CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:10]2[N:22]([C:25](=[O:42])[CH:26]([NH2:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:24][CH:9]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

3

反応物 1

HCID 675174094-(2-Benzyloxycarbonylamino-3,3-dimethyl-butyryl)-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 675062084-(2-Amino-3,3-dimethyl-butyryl)-3-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester収率 104.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution containing 46 (4.10 g, 7.02 mmol) and NH4OAc (275 mg, 3.50 mmol) in MeOH (70 mL) was treated with 10% Pd-on-carbon (wet, 745 mg, 0.70 mmol) and the stirred mixture was purged with hydrogen. After 3 h stirring under a balloon of hydrogen, TLC analysis (1:1 hexanes/EtOAc) indicated the reaction was complete. The catalyst was removed by filtration and the solvent was concentrated in vacuo. The residue was dissolved in Et2O and washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to provide 3.30 g of 47 as colorless oil which was used without further purification. Mass spectrum, m/z [449.9] (M+H)+.

後処理

  1. customthe stirred mixture was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe solvent was concentrated in vacuo
  4. dissolutionThe residue was dissolved in Et2O
  5. washwashed successively with saturated aqueous NaHCO3 and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-1ed52ad641504e6ba4de35564c6b0bbd
出典データセット
uspto-grants-2013_04
特許番号
US08415486B2

反応ノート

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