Lithium Hydroxide → HCID 9969831, compound

HRID 1006825Notes

Reaction equation

HRID 1006825 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([S:13]C(=O)C)[CH2:10][C@@H:9]1[CH2:17][O:18][CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([SH:13])[CH2:10][C@H:9]1[CH2:17][O:18][CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86584853HCID 86584853, compound

Product 1

HCID 9969831HCID 9969831, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.126 g (0.3 mmol) (2R,4S)-4-acetylsulfanyl-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester in 12 ml EtOH (degased with Ar) was treated at 0° C. with 0.9 ml 1N LiOH, warmed up to room temperature and stirred for 4.5 h. The reaction was recooled to 0° C. and quenched with aqueous 10% KHSO4. The reaction was extracted with aqueous 10% KHSO4/EtOAc (3×) and the organic phase was washed with aqueous 10% NaCl, dried over Na2SO4 and evaporated to give 0.11 g (97%) (2S,4R)-4-mercapto-2-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, MS: 378 (MH+).

Workup

  1. customwas recooled to 0° C.
  2. customquenched with aqueous 10% KHSO4
  3. extractionThe reaction was extracted with aqueous 10% KHSO4/EtOAc (3×)
  4. washthe organic phase was washed with aqueous 10% NaCl
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-71552985759641c8bfc22e980b0cb1f3
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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