Hydrochloric Acid → HCID 15814452, compound

HRID 2379284Notes

Reaction equation

HRID 2379284 reaction equation
[C:1]1([C:7]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([CH2:27][O:28][NH2:29])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:48](Cl)(=[O:50])[CH3:49].Cl>ClCCl.C(OCC)(=O)C>[C:36]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([CH2:27][O:28][NH:29][C:48](=[O:50])[CH3:49])[CH2:10]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 57078835(2S,4S)-4-triphenylmethylthio-2-aminooxymethyl-1-p-nitrobenzyloxycarbonylpyrrolidine2×

Product 1

HCID 15814452HCID 15814452, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-4-triphenylmethylthio-2-aminooxymethyl-1-p-nitrobenzyloxycarbonylpyrrolidine (6), prepared as above A (6), in dichloromethane are added pyridine (93 μl) and acetyl chloride (66 μl), and the mixture is stirred for 25 minutes. To the reaction mixture are added 1N-hydrochloric acid (1 ml) and ethyl acetate. The organic layer brine, dried over sodium sulfate, and concentrated in vacuo. The residue is purified by silica gel chromatography to give (2S,4S)-4-triphenylmethylthio-2-acetylaminooxymethyl-1-p-nitrobenzyloxycarbonylpyrrolidine (7:385 mg) as a pale yellow foam. Yield: 88%;.

Workup

  1. dry with materialThe organic layer brine, dried over sodium sulfate
  2. concentrationconcentrated in vacuo
  3. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-dcf96daeacce47efb6891158fc59d330
Source dataset
uspto-grants-1994_11
Patent number
US05360798

Reaction notes

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