Acetic Anhydride → HCID 9907496, compound

HRID 1058995Notes

Reaction equation

HRID 1058995 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:9][C@@H](C(OC)=O)[C@H:7]([CH2:14][N:15]=[N+]=[N-])[C@@H:6]1[CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:4].[C:27]([O:30][C:31](=[O:33])[CH3:32])(=O)C.[C:34](OCC)(=[O:36])[CH3:35]>[Pd]>[C:34]([NH:15][CH2:14][C@H:7]1[C@H:32]([C:31]([O:30][CH3:27])=[O:33])[CH2:9][C@H:5]([C:3]([OH:2])=[O:4])[C@H:6]1[CH2:18][NH:19][C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 57059424HCID 57059424, compound

Product 1

HCID 9907496HCID 9907496, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (±)-(1S,2S,3R,4R)-3-azidomethyl-2-(N-t-butoxycarbonylamino)methylcyclopentane-1,4-dicarboxylic acid dimethyl ester (386 mg, 1.04 mmole), acetic anhydride (0.25 mL) and palladium (25 mg, 10% on carbon) in 10 mL of ethyl acetate was stirred vigorously at room temperature under an hydrogen atmosphere. Upon completion, as determined by TLC, the reaction mixture was filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel using 75% ethyl acetate in hexanes to provide the title compound. (yield: 232 mg, 58%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel using 75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-cd81ac0173994c2bb510adff2c764950
Source dataset
uspto-grants-2003_02
Patent number
US06518305B1

Reaction notes

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