HCID 86593024, compound → HCID 86593023, compound

HRID 1815549Notes

Reaction equation

HRID 1815549 reaction equation
[CH2:1]([O:8][C:9]1[CH:48]=[CH:47][C:12]([CH2:13][C@H:14]([NH:35][C:36](=[O:46])[O:37][C@H:38]2[C@H:45]3[C@H:41]([O:42][CH2:43][CH2:44]3)[O:40][CH2:39]2)[C@H:15]([OH:34])[CH2:16][N:17]([CH2:30][CH:31]([CH3:33])[CH3:32])[S:18]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pt]>[NH2:27][C:24]1[CH:23]=[CH:22][C:21]([S:18]([N:17]([CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:16][C@@H:15]([OH:34])[C@@H:14]([NH:35][C:36](=[O:46])[O:37][C@H:38]2[C@H:45]3[C@H:41]([O:42][CH2:43][CH2:44]3)[O:40][CH2:39]2)[CH2:13][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:48][CH:47]=2)(=[O:19])=[O:20])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 86593024HCID 86593024, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86593023HCID 86593023, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of (3S,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-{isobutyl[(4-nitrophenyl)sulfonyl]amino}propylcarbamate (0.20 g, 0.29 mmol) in 3 mL of ethanol was added 64 mg of platinum (on activated carbon, 3% Pt). The mixture was stirred under an atmospheric pressure of hydrogen for 12 hours. The catalyst was filtered, and the solvent was removed under reduced pressure. The residue was purified on silica gel using ethyl acetate-hexanes (4:1) as eluent to provide 0.10 g (52%) of the title compound. 1H-NMR (DMSO-d6): δ 0.74 (3H,d), 0.81(3H,d), 1.19 (1H,m), 1.29(1H,m), 1.89 (1H, m), 2.34 (1H,t), 2.54-2.62 (2H,m), 2.71 (1H,m), 2.90 (2H,m), 3.22 (1H,d), 3.46 (1H,m), 3.52-3.59 (3H,m), 3.66 (1H,t) 3.83 (1H,dd), 4.80 (1H,q), 4.92 (1H,d,b), 4.99 (2H,s), 5.47 (1H,d), 5.94 (2H,s), 6.54 (2H,d), 6.81 (2H,d), 7.07(2H,d), 7.19 (1H,d), 7.28 (1H,d), 7.35 (5H,m). MS: 655 (M+).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-a4c2271e622d4e849517dda9e6233466
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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