Ammonia → HCID 86593026, compound

HRID 1815551Notes

Reaction equation

HRID 1815551 reaction equation
C([O:8][C:9]1[CH:51]=[CH:50][C:12]([CH2:13][C@H:14]2[C@@H:18]([CH2:19][N:20]([CH2:33][CH:34]([CH3:36])[CH3:35])[S:21]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)(=[O:23])=[O:22])[O:17][C:16]([CH3:38])([CH3:37])[N:15]2[C:39]([O:41][C@H:42]2[C@H:49]3[C@H:45]([O:46][CH2:47][CH2:48]3)[O:44][CH2:43]2)=[O:40])=[CH:11][CH:10]=1)C1C=CC=CC=1.N.[H][H]>CO.[Pd]>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([S:21]([N:20]([CH2:19][C@H:18]2[O:17][C:16]([CH3:37])([CH3:38])[N:15]([C:39]([O:41][C@H:42]3[C@H:49]4[C@H:45]([O:46][CH2:47][CH2:48]4)[O:44][CH2:43]3)=[O:40])[C@H:14]2[CH2:13][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:51][CH:50]=2)[CH2:33][CH:34]([CH3:36])[CH3:35])(=[O:22])=[O:23])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 86593025HCID 86593025, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86593026HCID 86593026, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (3S,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (4S,5R)-4-[4-(benzyloxy)benzyl]-5-({isobutyl[(4-nitrophenyl)sulfonyl]amino}methyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate. (0.18 g, 0.25 mmol) in 6 mL of a 2M solution of ammonia in methanol was added 0.18 g of palladium (on charcoal, 10% Pd, Degussa type). 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 (7:3) as eluent to provide 81 mg (54%) of the title compound. 1H-NMR (DMSO-d6): δ 0.76 (3H,d), 0.80 (3H,d), 1.19,1.33 (3H,s)*, 1.44, 1.50 (3H,s)*, 1.74 (2H,m), 1.89 (1H,m), 2.49-2.75 (6H,m), 2.89-2.99 (2H,m), 3.19 (1H,m), 3.61 (2H,m), 3.80 (1H,m), 4.07 (1H,m), 4.74 (1H,q), 5.50,5.54 (1H,d)*, 5.94 (2H,s,b), 6.54 (2H,d), 6.64 (2H,d), 6.93,6.99 (2H,d)*, 7.13,7.20 (2H,d)*, 9.20, 9.22 (1H,s)*. MS: 605 (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-695ac794bc144bf89a6e0c6bd1a25fef
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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