1-Hydroxybenzotriazole → (S)-tert-butyl 2-amino-2-oxo-1-phenylethylcarbamate

HRID 2269651Notes

Reaction equation

HRID 2269651 reaction equation
[C:1]([O:5][C:6]([N:8](C1C=CC=CC=1)[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.N.[CH:21]1[CH:22]=[CH:23][C:24]2N(O)N=N[C:25]=2[CH:26]=1.CC[N:33]=C=NCCCN(C)C.Cl>ClCCl>[NH:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:10]([NH2:33])=[O:12])[C:25]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:26]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12896473Azane;hydrateHCID 21905636N-(tert-Butoxycarbonyl)-N-phenylglycine

Product 1

HCID 11128727(S)-tert-butyl 2-amino-2-oxo-1-phenylethylcarbamateYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a dichloromethane solution containing 4.3 g of N-(tert-butoxycarbonyl)phenylglycine, 5 ml of ammonia water, 1.5 g of HOBt and 23 g of EDC hydrochloride were added under ice cooling and the resultant mixture was stirred overnight at room temperature. The reaction mixture was treated similarly to that in Example 144 (Process 2) to give 0.42 g of the title compound.

Workup

  1. additionwere added under ice cooling
  2. additionThe reaction mixture was treated similarly to that in Example 144 (Process 2)

Sources & evidence

ORD record
ord-213ec1f4a11b4962b222d46e87d72f15
Source dataset
uspto-grants-2001_12
Patent number
US06329502B1

Reaction notes

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