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Carbamic acid, ethyl ester → Ethoxycarbonyl-(1-benzotriazolyl)glycine

HRID 2338
Notes
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Reaction equation

HRID 2338 reaction equation
[C:1](=[O:6])([O:3][CH2:4][CH3:5])[NH2:2].O.[C:8]([OH:12])(=[O:11])[CH:9]=O.[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1>C1(C)C=CC=CC=1>[CH2:4]([O:3][C:1]([N:2]([N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1)[CH2:9][C:8]([OH:12])=[O:11])=[O:6])[CH3:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5641Carbamic acid, ethyl esterHCID 15620607Glyoxylic acid, monohydrateHCID 178418385HCID 178418385, compound

Product 1

HCID 53982471Ethoxycarbonyl-(1-benzotriazolyl)glycineYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
15 °C

Procedure

Ethyl carbamate (69.0 g, 774.5 mmol), glyoxylic acid hydrate (71.3 g, 774.5 mmol) and benzotriazole (92.0 g, 774.5 mmol) were dissolved in toluene (2.3 1) and the mixture was heated with distillation for 3 h to precipitate the product. The mixture was diluted with toluene (totally 2.3 1) and stirred at 15° C. overnight. The resultant precipitate was collected by filtration, washed with toluene (160 ml) and dried to afford the title compound (196.06 g, 96%): mp. 189°-192° C.

Workup

  1. temperaturethe mixture was heated with distillation for 3 h
  2. customto precipitate the product
  3. additionThe mixture was diluted with toluene (totally 2.3 1) and
  4. filtrationThe resultant precipitate was collected by filtration
  5. washwashed with toluene (160 ml)
  6. customdried

Sources & evidence

ORD record
ord-5df61b0f843d454b91abd7c3ea08a12b
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728829

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes