p-Toluenesulfonic acid → HCID 22859270, compound

HRID 1439969Notes

Reaction equation

HRID 1439969 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([NH:22][C@@H:23]([CH2:28][CH2:29][CH2:30][OH:31])[C:24](OC)=[O:25])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([NH:22][C@H:23]1[CH2:28][CH2:29][CH2:30][O:31][C:24]1=[O:25])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54140200HCID 54140200, compound

Product 1

HCID 22859270HCID 22859270, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In benzene (100 ml ) was dissolved methyl (S )-2-[[N-benzyloxycarbonyl-(L )-phenylalanyl]amino]-5-hydroxyvalerate (2.85 g) followed by addition of p-toluenesulfonic acid (0.09 g), and the mixture was stirred under reflux for 1 hour. The reaction mixture was concentrated under reduced pressure to provide (S)-3-[[N-benzyloxycarbonyl-(L)-phenylalanyl]amino]-2-oxotetrahydropyran (chemical formula below) (2.0 g, 77%) m p 167°-169° C. optical rotation [α]D +43. 6° (c=0.50, CHCl3) ##STR36##

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-50db9f6343be4f60bed470c898bffd7d
Source dataset
uspto-grants-1996_03
Patent number
US05496834

Reaction notes

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