Hydrochloric Acid → HCID 15814452, compound

HRID 260000Notes

Reaction equation

HRID 260000 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 above as 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 is taken, washed with water, aqueous sodium hydrogen carbonate, and 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. washwashed with water, aqueous sodium hydrogen carbonate, and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-4a3cd2294a9d48f289b83a2338e2cde6
Source dataset
uspto-grants-1996_06
Patent number
US05523415

Reaction notes

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