Benzyl chloroformate → N-(Carboxymethyl)-N-((phenylmethoxy)carbonyl)glycine

HRID 979178Notes

Reaction equation

HRID 979178 reaction equation
O.[NH:2]([CH2:7][C:8]([O-:10])=[O:9])[CH2:3][C:4]([O-:6])=[O:5].[Na+].[Na+].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].[OH-].[Na+]>O>[CH2:17]([O:16][C:14]([N:2]([CH2:7][C:8]([OH:10])=[O:9])[CH2:3][C:4]([OH:6])=[O:5])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 12520792Sodium iminodiacetate dibasic monohydrate

Product 1

HCID 10107013N-(Carboxymethyl)-N-((phenylmethoxy)carbonyl)glycineYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Disodium iminodiacetate monohydrate (11.7 g, 0.060 m) was dissolved in water (40 ml) and cooled to 0°. Benzyl chloroformate (13.3 g, 0.078 m) was added in portions as the pH of the solution was kept at 9-12 by addition of 2N sodium hydroxide solution as needed. When addition was complete the mixture was stirred an additional 3 hours at 0°-10° C., then extracted with diethyl ether. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate and concentrated to give 13.0 g (81%) of N-benzyloxycarbonyliminodiacetic acid (V-C).

Workup

  1. temperaturecooled to 0°
  2. additionWhen addition
  3. extractionextracted with diethyl ether
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e72711a0d92e4e1c8faa1425e38c9926
Source dataset
uspto-grants-1987_05
Patent number
US04666906

Reaction notes

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