Ammonia → tert-Butyl (1R)-2-amino-1-(1H-indol-3-ylmethyl)-2-oxoethylcarbamate

HRID 1355582Notes

Reaction equation

HRID 1355582 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:24]>CO>[NH2:24][C:10](=[O:11])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 7188267N-[(1,1-Dimethylethoxy)carbonyl]-D-tryptophan methyl ester

Product 1

HCID 57107549tert-Butyl (1R)-2-amino-1-(1H-indol-3-ylmethyl)-2-oxoethylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

In a reactor under 200 psi of pressure was added (6.2 g, 22 mmol) of methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoate and 120 ml of methanol saturated with NH3. The solution was stirred at about 85° C. for about 24 hours. After cooling, the solution was evaporated and the residue precipitated by the addition of diisopropyl ether. Filtration gave 5.4 g of the title product as a white powder. Melting point: 142-143° C.

Workup

  1. temperatureAfter cooling
  2. customthe solution was evaporated
  3. customthe residue precipitated by the addition of diisopropyl ether
  4. filtrationFiltration

Sources & evidence

ORD record
ord-d3d735e5b93243689b162e748a1c30d3
Source dataset
uspto-grants-2003_07
Patent number
US06586445B1

Reaction notes

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