Sodium Thiosulfate → 2-oxo-3(S)-{3-(pyridin-3-ylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1(s)-(4-fluorophenyl)ethylamino]-propionylamino}hexanoic acid cyclopropylamide

HRID 907653Notes

Reaction equation

HRID 907653 reaction equation
[CH:1]1([NH:4][C:5](=[O:40])[CH:6]([OH:39])[C@@H:7]([NH:11][C:12](=[O:38])[C@@H:13]([NH:25][C@@H:26]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[C:27]([F:30])([F:29])[F:28])[CH2:14][S:15]([CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:17])=[O:16])[CH2:8][CH2:9][CH3:10])[CH2:3][CH2:2]1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:1]1([NH:4][C:5](=[O:40])[C:6](=[O:39])[C@@H:7]([NH:11][C:12](=[O:38])[C@@H:13]([NH:25][C@@H:26]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[C:27]([F:28])([F:29])[F:30])[CH2:14][S:15]([CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:16])=[O:17])[CH2:8][CH2:9][CH3:10])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 24477Sodium ThiosulfateHCID 596090592-hydroxy-3(S)-{3-(pyridin-3-ylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1(S)-(4-fluorophenyl)ethylamino]propionylamino} hexanoic acid cyclopropylamide

Product 1

HCID 575620912-oxo-3(S)-{3-(pyridin-3-ylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1(s)-(4-fluorophenyl)ethylamino]-propionylamino}hexanoic acid cyclopropylamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-hydroxy-3(S)-{3-(pyridin-3-ylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1(S)-(4-fluorophenyl)ethylamino]propionylamino}hexanoic acid cyclopropylamide (590 mg, 1 mmol) in methylene chloride, DMP was added slowly. The reaction mixture was stirred at room temperature for 30 min and then a 0.26 M Na2S2O3 in sat. NaHCO3 was added. The reaction mixture was stirred for 20 min. The aqueous layer was extracted with methylene chloride and the combined organic extracts were dried over MgSO4, filtered and concentrated to give 2-oxo-3(S)-{3-(pyridin-3-ylmethanesulfonyl)-2(R)-[2,2,2-trifluoro-1(S)-(4-fluorophenyl)ethylamino]-propionylamino}hexanoic acid cyclopropylamide which was purified by flash column (2% MeOH—CH2Cl2) to give pure product as a yellow solid.

Workup

  1. stirringThe reaction mixture was stirred for 20 min
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd37fa82eb1f44ff8e539aa51a48af62
Source dataset
uspto-grants-2011_09
Patent number
US08013183B2

Reaction notes

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