Water → Benzyl N-(tert-butoxycarbonyl)glycinate

HRID 2118834Notes

Reaction equation

HRID 2118834 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)(O)[O-].[K+].O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516893Potassium Bicarbonate

Product 1

HCID 357720Benzyl N-(tert-butoxycarbonyl)glycinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-5 °C

Procedure

N-(t-Butoxycarbonyl)glycine (8.75 g, 0.05 mole) and benzyl bromide (9.4 g, 0.055 mole) were slurried in 20 ml of dimethylformamide and treated with 6.0 g (0.06 mole) of potassium bicarbonate under argon. After stirring for 38 hours, water was added to give a mass of chunky white solid which was filtered and washed with water. The solid was taken up in ethyl acetate, dried (sodium sulfate), evaporated to a solid, and recrystallized from 600 ml of hot hexane. Cooling to -5° C. for two hours and filtering gave 11.6 g of crystalline flakes, melting point 72°-73° C., in two crops.

Workup

  1. customto give a mass of chunky white solid which
  2. filtrationwas filtered
  3. washwashed with water
  4. dry with materialdried (sodium sulfate)
  5. customevaporated to a solid
  6. customrecrystallized from 600 ml of hot hexane
  7. filtrationfiltering
  8. customgave 11.6 g of crystalline flakes, melting point 72°-73° C.

Sources & evidence

ORD record
ord-152b2bf013c74d7d861c7fc1aff73c12
Source dataset
uspto-grants-1987_07
Patent number
US04680388

Reaction notes

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