Lithium Hydroxide → [(1-Biphenyl-4-yl-ethyl)-tert-butoxycarbonyl-amino]-acetic acid

HRID 1178158Notes

Reaction equation

HRID 1178158 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:29])[CH2:6][N:7]([CH:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)[CH3:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>C1COCC1.CO.O>[C:20]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:19]=[CH:18][C:17]([CH:15]([N:7]([CH2:6][C:5]([OH:29])=[O:4])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:16])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59559672[(1-Biphenyl-4-yl-ethyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester

Product 1

HCID 59559653[(1-Biphenyl-4-yl-ethyl)-tert-butoxycarbonyl-amino]-acetic acidYield 99%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (140 mg, 3.3 mmol) was added to a stirred solution of [(1-biphenyl-4-yl-ethyl)-tert-butoxycarbonyl-amino]-acetic acid methyl ester (202 mg, 0.54 mmol) in THF:MeOH:H2O (3:1:1, 10 mL), and the resulting mixture was stirred at room temperature for 12 hrs. The reaction mixture was concentrated under reduced pressure. Cold water was then added, the product was acidified with aqueous citric acid solution and then extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 190 mg (97.9% yield) of [(1-biphenyl-4-yl-ethyl)-tert-butoxycarbonyl-amino]-acetic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionCold water was then added
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bfb1c9103d1f4b3ca43ed362a6fb5848
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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