Sodium Hydroxide → HCID 72950364, compound

HRID 1526765Notes

Reaction equation

HRID 1526765 reaction equation
Cl.[NH2:2][CH:3]([C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[C:12]([Br:20])[CH:11]=1)[CH2:4][C:5]([O:7]CC)=[O:6].[OH-].[Na+].OP([O-])(O)=O.[K+]>O>[NH2:2][C@H:3]([C:10]1[CH:15]=[C:14]([C:16]([CH3:18])([CH3:17])[CH3:19])[CH:13]=[C:12]([Br:20])[CH:11]=1)[CH2:4][C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516951Monobasic potassium phosphateHCID 86709931HCID 86709931, compound

Product 1

HCID 72950364HCID 72950364, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of ethyl 3-amino-3-(3-bromo-5-tert-butylphenyl)-propionate hydrochloride (125 g, 0.38 mol) in water (500 mL) was basified with 2.5 N NaOH (pH ˜12) by drop-wise addition to give a creamy oily residue. The pH of the aqueous layer was adjusted to pH=8.2 by the addition of 50 mM KH2PO4 solution. Amano lipase PS (75 g) was added to above reaction mixture and the reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered and the solid was washed with ethyl acetate to give a colorless solid of the resolved (S)-acid (37 g).

Workup

  1. customto give a creamy oily residue
  2. additionAmano lipase PS (75 g) was added to above reaction mixture
  3. filtrationThe reaction mixture was filtered
  4. washthe solid was washed with ethyl acetate
  5. customto give a colorless solid of the resolved (S)-acid (37 g)

Sources & evidence

ORD record
ord-9c88b552838c4666a5eb9e0896354fd7
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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