Water → N-{(1S)-1-[2'-chloro-4'-(methylsulfonyl)biphenyl-4-yl]-2,2,2-trifluoroethyl}-4-fluoro-L-leucine

HRID 239859Notes

Reaction equation

HRID 239859 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([NH:23][C@H:24]([C:30]([O:32]CC)=[O:31])[CH2:25][C:26]([F:29])([CH3:28])[CH3:27])[C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1.O1CCCC1.O.[OH-].[Li+]>[Cl-].[Na+].O.C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([NH:23][C@H:24]([C:30]([OH:32])=[O:31])[CH2:25][C:26]([F:29])([CH3:28])[CH3:27])[C:19]([F:21])([F:22])[F:20])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68774733ethyl N-{(1S)-1-[2'-chloro-4'-(methylsulfonyl)biphenyl-4-yl]-2,2,2-trifluoroethyl}-4-fluoro-L-leucinate

Product 1

HCID 68444063N-{(1S)-1-[2'-chloro-4'-(methylsulfonyl)biphenyl-4-yl]-2,2,2-trifluoroethyl}-4-fluoro-L-leucine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of ethyl N-{(1S)-1-[2′-chloro-4′-(methylsulfonyl)biphenyl-4-yl]-2,2,2-trifluoroethyl}-4-fluoro-L-leucinate in a 3:1:1 mixture (0.1 M) of tetrahydrofuran, water and ethanol was added solid Lithium Hydroxide. The reaction was stirred for 64 h at room temperature and heated for one hour at 38° C. after which TLC analysis indicated disappearance of starting material. The reaction was cooled and treated with aqueous pH 5 NaH2PO4 solution and brine and then 1N aqueous HCL until pH 2. The phases were separated and the organic phase was washed with aqueous pH 5 NaH2PO4 solution and brine.

Workup

  1. temperatureheated for one hour at 38° C. after which TLC analysis
  2. temperatureThe reaction was cooled
  3. customThe phases were separated
  4. washthe organic phase was washed with aqueous pH 5 NaH2PO4 solution and brine

Sources & evidence

ORD record
ord-1ebb728a76fd4b4799fb0f5e34016cb0
Source dataset
uspto-grants-2014_02
Patent number
US08642799B2

Reaction notes

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