(2S,3R)-(4-Cyano-2,2-dimethylbutyl)-[3-((3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-carbamic acid benzyl ester → [(1S, 2R)-1-Benzyl-3-(4-cyano-2,2-dimethylbutylamino)-2-hydroxy-propyl]-carbamic acid (3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yl ester

HRID 2117699Notes

Reaction equation

HRID 2117699 reaction equation
C(OC(=O)[N:10]([CH2:34][C:35]([CH3:41])([CH3:40])[CH2:36][CH2:37][C:38]#[N:39])[CH2:11][C@H:12]([OH:33])[C@H:13]([NH:21][C:22]([O:24][C@@H:25]1[C@H:32]2[C@H:28]([O:29][CH2:30][CH2:31]2)[O:27][CH2:26]1)=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1.[H][H]>CCOC(C)=O.[Pd]>[O:27]1[C@H:28]2[O:29][CH2:30][CH2:31][C@H:32]2[C@@H:25]([O:24][C:22](=[O:23])[NH:21][C@@H:13]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C@H:12]([OH:33])[CH2:11][NH:10][CH2:34][C:35]([CH3:40])([CH3:41])[CH2:36][CH2:37][C:38]#[N:39])[CH2:26]1

Participants

5

Reactant 2

HCID 67091837(2S,3R)-(4-Cyano-2,2-dimethylbutyl)-[3-((3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-carbamic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 59815752[(1S, 2R)-1-Benzyl-3-(4-cyano-2,2-dimethylbutylamino)-2-hydroxy-propyl]-carbamic acid (3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2S,3R)-(4-Cyano-2,2-dimethylbutyl)-[3-((3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yloxycarbonylamino)-2-hydroxy-4-phenyl-butyl]-carbamic acid benzyl ester (0.740 g, 1.28 mmol) in EtOAc at ambient temperature was treated with 10% palladium on carbon (0.075g) and stirred under a balloon of hydrogen. After stirring 16 h the mixture was filtered and solvent was removed in vacuo to give desired product as a colorless oil.

Workup

  1. filtrationwas filtered
  2. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-23ee1261122848a1b47ec1a4d50ecf5c
Source dataset
uspto-grants-2008_10
Patent number
US07442718B2

Reaction notes

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