Ammonia → BOC-Nva-Met-NH2

HRID 851722Notes

Reaction equation

HRID 851722 reaction equation
[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([C:6]([NH:8][C@H:9]([C:14](OC)=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=[O:7])[CH2:3][CH2:4][CH3:5].[NH3:25]>CO>[C:21]([O:20][C:18]([NH:1][C@H:2]([C:6]([NH:8][C@H:9]([C:14]([NH2:25])=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=[O:7])[CH2:3][CH2:4][CH3:5])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57129312BOC-Nva-Met-OMe

Product 1

HCID 57006973BOC-Nva-Met-NH2

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.81 g (5 mmoles) of BOC-Nva-Met-OMe are dissolved in 20 ml of methanol, and gaseous ammonia is introduced into the solution for 0.5 hours under ice cooling. The reaction mixture is allowed to stand at room temperature overnight, and then stored in a cold place for some hours. The separated crystalline product is filtered off to obtain 1.27 g of the desired product. The filtrate is evaporated, and the residue is recrystallized from 5 ml of ethanol to obtain further 0.35 g of the product. Thus 1.62 g (93%) of BOC-Nva-Met-NH2 are obtained; m.p.: 166°-167° C., Rf2 =0.57, [α]D25 =-40.9° (c=1%, in methanol).

Workup

  1. waitstored in a cold place for some hours
  2. filtrationThe separated crystalline product is filtered off

Sources & evidence

ORD record
ord-1b9055973adf431eb7700a171389b852
Source dataset
uspto-grants-1983_05
Patent number
US04386073

Reaction notes

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