Acetic Anhydride → HCID 15671530, compound

HRID 1088287Notes

Reaction equation

HRID 1088287 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:14][C@H:13]2[CH2:25][CH2:26][OH:27])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1.C(OCC)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][Si:18]([C:21]([CH3:23])([CH3:24])[CH3:22])([CH3:20])[CH3:19])[CH2:14][C@H:13]2[CH2:25][CH2:26][O:27][C:30](=[O:32])[CH3:31])=[O:11])=[CH:28][CH:29]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 15671484HCID 15671484, compound

Product 1

HCID 15671530HCID 15671530, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

(2R,4R)-1-p-Nitrobenzyloxycarbonyl-2-(2-hydroxyethyl)-4-t-butyldimethylsilyloxypyrrolidine (900 mg) was dissolved in 2.25 ml of dry pyridine, and 2.25 ml of acetic anhydride was added to the solution at room temperature, followed by stirring for 1 hour. The reaction mixture was diluted with diethyl ether, washed successively with brine, a diluted aqueous hydrochloric acid, brine, a diluted aqueous sodium hydroxide solution and brine, dired over anhydrous sodium sulfate to give (2R,4R)-1-p-nitrobenzyloxycarbonyl-2-(2-acetoxyethyl)-4-t-butyldimethylsilyloxypyrrolidine.

Workup

  1. washwashed successively with brine

Sources & evidence

ORD record
ord-b87da8cadd4a4be0bf84bb48265de7d5
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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