Lithium Hydroxide → HCID 68731246, compound

HRID 1523232Notes

Reaction equation

HRID 1523232 reaction equation
[CH3:1][C:2]([CH3:20])([S@@:4]([NH:6][C@:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:13])[CH2:8][C:9]([O:11]C)=[O:10])=[O:5])[CH3:3].[Li+].[OH-]>CO.O.CO.O>[CH3:3][C:2]([CH3:20])([S@@:4]([NH:6][C@:7]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([CH3:13])[CH2:8][C:9]([OH:11])=[O:10])=[O:5])[CH3:1]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 68731966HCID 68731966, compound

Product 1

HCID 68731246HCID 68731246, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (R)-methyl 3-((S)-1,1-dimethylethylsulfinamido)-3-phenylbutanoate (280 mg, 0.94 mmol) in MeOH (2 mL) and H2O (0.5 mL) was added LiOH (138 mg, 3.29 mmol). The solution was stirred for 4 h and then concentrated to give the residue. The residue was dissolved in 15% MeOH/H2O and filtered to give (R)-3-((S)-1,1-dimethylethylsulfinamido)-3-phenylbutanoic acid (266 mg, 100%). 1H NMR (CDCl3): 1.10 (s, 9H), 1.51 (s, 3H), 2.43-2.52 (d, 1H), 2.73-2.86 (d, 1H), 7.15-7.18 (m, 1H), 7.06-7.12 (m, 3H), 7.30-7.40 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customto give the residue
  3. filtrationfiltered

Sources & evidence

ORD record
ord-003662a6d4a0481e91d2d1b027cb82b7
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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