HCID 61600402, compound → N-Boc-N-isopropylamino-acetic acid

HRID 891702Notes

Reaction equation

HRID 891702 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:6]([CH3:8])[CH3:7]>CO>[C:12]([O:11][C:9]([N:5]([CH2:4][C:3]([OH:16])=[O:2])[CH:6]([CH3:8])[CH3:7])=[O:10])([CH3:13])([CH3:15])[CH3:14]

Participants

3

Reactant 1

HCID 61600402HCID 61600402, compound

Product 1

HCID 10465935N-Boc-N-isopropylamino-acetic acidYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (N-t-butoxycarbonyl-N-isopropyl-amino)-acetic acid methyl ester (5.59 g, 24.2 mmol) in a mixture of methanol (112 ml) and distilled water (56 ml) was added 1M aqueous sodium hydroxide solution (37 ml) in an ice bath, and the mixture was stirred at room temperature for 7 hours. After checking the completion of the reaction, Dowex-50W was added thereto in the ice bath to adjust the pH of the reaction mixture to 5 to 4. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to give (N-t-butoxycarbonyl-N-isopropyl-amino)acetic acid (5.25 g) as a crude product.

Workup

  1. distillationdistilled water (56 ml)
  2. additionwas added 1M aqueous sodium hydroxide solution (37 ml) in an ice bath
  3. customthe completion of the reaction, Dowex-50W
  4. additionwas added
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-e752b2e142ac40bd9dd558bb24c6a7d7
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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