4-Toluenesulfonyl chloride → HCID 86749232, compound

HRID 375985Notes

Reaction equation

HRID 375985 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@@H:13]([OH:18])[C:14]([O:16][CH3:17])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>N1C=CC=CC=1.O.CN(C1C=CC=CN=1)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C@@H:13]([O:18][S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)(=[O:34])=[O:33])[C:14]([O:16][CH3:17])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11046151HCID 11046151, compound

Product 1

HCID 86749232HCID 86749232, compoundYield 112.1%

Reagents, catalysts & solvents 3

HCID 218852-DimethylaminopyridineCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

20 g of methyl N-benzyloxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenylbutyrate was dissolved in 100 ml of pyridine and 13.3 g of p-toluenesulfonyl chloride was added thereto while maintaining the reaction temperature at 10° to 20° C. Next, 0.03 g of dimethylaminopyridine (DMAP) was added thereto as a catalyst and the mixture was stirred at 20° to 25° C. for 5 hours. Then the reaction mixture was diluted with 500 ml of water and extracted with 150 ml portions of ethyl acetate twice. The extract was washed successively with 50 ml of 2 N hydrochloric acid and 50 ml of a saturated aqueous solution of sodium chloride, dehydrated over anhydrous sodium sulfate and filtered. After distilling off the solvent, 32.5 g of methyl N-benzyloxycarbonyl-3(S)-amino-2(R)-p-toluenesulfonyloxy-4-phenylbutyrate was obtained as a pale yellow, oily substance.

Workup

  1. temperaturewhile maintaining the reaction temperature at 10° to 20° C
  2. extractionextracted with 150 ml portions of ethyl acetate twice
  3. washThe extract was washed successively with 50 ml of 2 N hydrochloric acid and 50 ml of a saturated aqueous solution of sodium chloride
  4. filtrationfiltered
  5. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-c324af98913f40b6bfa66fb8fc750705
Source dataset
uspto-grants-1996_01
Patent number
US05488118

Reaction notes

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