Ammonia → BOC-Nva-Leu-NH2

HRID 851717Notes

Reaction equation

HRID 851717 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][CH:11]([CH3:13])[CH3:12])=[O:7])[CH2:3][CH2:4][CH3:5].[NH3:25]>CO>[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]([NH2:25])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 57262488BOC-Nva-Leu-OMe

Product 1

HCID 57077739BOC-Nva-Leu-NH2Yield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.0 g (14.5 mmoles) of BOC-Nva-Leu-OMe are dissolved in 50 ml of methanol, and gaseous ammonia is introduced into the solution for 0.5 hours under ice cooling. The solution is allowed to stand at room temperature overnight, then cooled again, saturated with gaseous ammonia, and evaporated after 4 hours of standing. The crystalline residue is recrystallized from a mixture of ethyl acetate and ether. 4.37 g (91%) of BOC-Nva-Leu-NH2 are obtained; m.p.: 158°-159° C., Rf2 =0.60, [α]D25 =-48.7° (c=1%, in methanol).

Workup

  1. customevaporated after 4 hours
  2. customThe crystalline residue is recrystallized from a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-f3b74040e8974f2ebfa9b6228397ce39
Source dataset
uspto-grants-1983_05
Patent number
US04386073

Reaction notes

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