Sarcosine → N-Carbobenzoxysarcosine

HRID 863788Notes

Reaction equation

HRID 863788 reaction equation
[CH3:1][NH:2][CH2:3][C:4]([OH:6])=[O:5].C(=O)(O)[O-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>O>[CH2:16]([O:15][C:13]([N:2]([CH3:1])[CH2:3][C:4]([OH:6])=[O:5])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1088SarcosineHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 97053N-Carbobenzoxysarcosine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

N-methylglycine (7.0 g) was added to water (50 ml) and the pH of the solution adjusted to 9 with solid sodium bicarbonate. The solution was cooled to 0° C. and stirred vigorously, while benzyl chloroformate (19 ml) was added dropwise over 20 minutes. The mixture was stirred for a further 2 hours at 0° C. and an additional 2 hours at room temperature, then extracted with diethyl ether (2×130 ml). The aqueous solution was then acidified to pH 3 with 5N HCl and the product isolated by extraction with ethyl acetate (2×130 ml). The combined organic extracts were dried over anhydrous sodium sulphate and the solution concentrated in vacuo to give N-(benzyloxycarbonyl)-N-methylglycine as a pale yellow oil (16.2 g).

Workup

  1. additionwas added dropwise over 20 minutes
  2. extractionextracted with diethyl ether (2×130 ml)
  3. customthe product isolated by extraction with ethyl acetate (2×130 ml)
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
  5. concentrationthe solution concentrated in vacuo

Sources & evidence

ORD record
ord-9ce9b02515c34255b97f218f148208a1
Source dataset
uspto-grants-1996_10
Patent number
US05561133

Reaction notes

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