Hydrochloric Acid → N-Boc-N-(2-phenylethyl)glycine

HRID 1597638Notes

Reaction equation

HRID 1597638 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][N:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.[Li+].[OH-].CO.Cl>O.CCOC(C)=O>[C:18]([O:17][C:15]([N:6]([CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:5][C:4]([OH:22])=[O:3])=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 21699745HCID 21699745, compound

Product 1

HCID 10588743N-Boc-N-(2-phenylethyl)glycine

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

A solution of the ester 14-1 (1.7 g, 5.5 mmol), 11.1 mL 1N LiOH and 11 mL MeOH was stirred at room temperature for 16 h. The mixture was poured into water/EtOAc and acidified with 1N HCl to pH≈3. After extraction with EtOAc (2×), the organic layers were washed with brine, dried (MgSO4) and evaporated to give 14-2 as a foam which was used as such in the next step.

Workup

  1. extractionAfter extraction with EtOAc (2×)
  2. washthe organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-3308fe69c76240b9ab2c3cddf32527a2
Source dataset
uspto-grants-2001_09
Patent number
US06294549B1

Reaction notes

Loading…