Water → HCID 69462867, compound

HRID 1371295Notes

Reaction equation

HRID 1371295 reaction equation
[C:1]1([O:11][CH2:12][C:13]([N:15]2[C@H:19]([C:20]([O:22]C)=[O:21])[CH2:18][S:17][CH:16]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O.[Li+].[OH-]>O1CCOCC1>[C:1]1([O:11][CH2:12][C:13]([N:15]2[C@H:19]([C:20]([OH:22])=[O:21])[CH2:18][S:17][CH:16]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 69904869HCID 69904869, compound

Product 1

HCID 69462867HCID 69462867, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2RS,4R)-3-((1-naphthyloxy)acetyl)-2-phenylthiazolidine-4-carboxylic acid, methyl ester (2.50 g, 6.14 mmol) in dioxane(15 mL)-water(5.0 mL) at room temperature was added 1.0 N LiOH solution (6.75 mL, 6.75 mmol). After stirring at room temperature for 16 hrs, The mixture was partitioned between EtOAc-5% KHSO4. The organic phase was washed with saturated NaCl solution, dried over anhydrous Na2SO4 and evaporated to give the title compound (2.42 g, 100%) as a viscous oil. TLC(MeOH-CH2Cl2; 1:9) Rf=0.38.

Workup

  1. customThe mixture was partitioned between EtOAc-5% KHSO4
  2. washThe organic phase was washed with saturated NaCl solution
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-4ec8a9cf434e4224b2f663adcd72d7ec
Source dataset
uspto-grants-2007_01
Patent number
US07157430B2

Reaction notes

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