Benzyl carbamate → (1H-Benzotriazol-1-yl){[(benzyloxy)carbonyl]amino}acetic acid

HRID 1642087Notes

Reaction equation

HRID 1642087 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[N:8]1.[C:16](=[O:26])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH2:17]>C1(C)C=CC=CC=1>[N:7]1([CH:3]([NH:17][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:26])[C:2]([OH:6])=[O:5])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[N:8]1

Participants

5

Reactant 3

HCID 12136Benzyl carbamateHCID 15620607Glyoxylic acid, monohydrateHCID 178418385HCID 178418385, compound

Product 1

HCID 4315963(1H-Benzotriazol-1-yl){[(benzyloxy)carbonyl]amino}acetic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of glyoxylic acid monohydrate (4.60 g), benzotriazole (5.95 g) and benzyl carbamate (7.55 g) was heated to reflux in toluene (100 ml) for 18 h, under Dean-Stark conditions. The mixture was then allowed to cool to room temperature, and the resulting precipitate collected by filtration. This was then recrystallised from diethyl ether giving an off-white solid (11.66 g)

Workup

  1. temperaturewas heated
  2. filtrationthe resulting precipitate collected by filtration
  3. customThis was then recrystallised from diethyl ether giving an off-white solid (11.66 g)

Sources & evidence

ORD record
ord-0262d2eb8921458aba46839a8f45e9dc
Source dataset
uspto-grants-2012_02
Patent number
US08119630B2

Reaction notes

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