Hydrochloric Acid → N-(benzylsulfonyl)-D-isoleucyl-L-methionine

HRID 890927Notes

Reaction equation

HRID 890927 reaction equation
C[O:2][C:3](=[O:28])[C@H:4]([CH2:24][CH2:25][S:26][CH3:27])[NH:5][C:6](=[O:23])[C@@H:7]([C@@H:19]([CH2:21][CH3:22])[CH3:20])[NH:8][S:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:11])=[O:10].Cl>C(O)C.[OH-].[Na+]>[CH2:12]([S:9]([NH:8][C@@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:28])=[O:2])[CH2:24][CH2:25][S:26][CH3:27])=[O:23])[C@@H:19]([CH2:21][CH3:22])[CH3:20])(=[O:11])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69623705N-(benzylsulfonyl)-D-isoleucyl-L-methionine methyl ester

Product 1

HCID 69623728N-(benzylsulfonyl)-D-isoleucyl-L-methionineYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of N-(benzylsulfonyl)-D-isoleucyl-L-methionine methyl ester (6.4 g, 14.9 mmol) in ethanol (30 ml), 2N aqueous sodium hydroxide (30 ml) was added and stirred at room temperature. After 1 hour, the reaction mixture was adjusted to pH 2 with 2N aqueous hydrogen chloride and then extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off and the filtrate was concentrated under reduced pressure to give N-(benzylsulfonyl)-D-isoleucyl-L-methionine (6.2 g, 14.9 mmol; yield 100%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationMagnesium sulfate was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f200889d87434159b73a781ca6fa1ad2
Source dataset
uspto-grants-2006_02
Patent number
US07001887B2

Reaction notes

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