Ethyl chloroformate → 3-[2-(N-t-butoxycarbonylglycyl)hydrazino]-5-methyl-6-phenyl-1,2,4-triazine

HRID 2290354Notes

Reaction equation

HRID 2290354 reaction equation
ClC(OCC)=O.[C:7]([O:11][C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].[NH:19]([C:21]1[N:22]=[N:23][C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:25]([CH3:27])[N:26]=1)[NH2:20]>C(Cl)Cl>[C:7]([O:11][C:12]([NH:14][CH2:15][C:16]([NH:20][NH:19][C:21]1[N:22]=[N:23][C:24]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:25]([CH3:27])[N:26]=1)=[O:18])=[O:13])([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 155864093-Hydrazino-5-methyl-6-phenyl-1,2,4-triazine

Product 1

HCID 202320773-[2-(N-t-butoxycarbonylglycyl)hydrazino]-5-methyl-6-phenyl-1,2,4-triazineYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction of ethyl chloroformate (2.441 g) with N-t-butoxycarbonylglycine (3.938 g) in methylene chloride under ice cooling gave a solution comprising the mixed acid anhydride, which was reacted with 3-hydrazino-5-methyl-6-phenyl-1,2,4-triazine (3.015 g) in a similar manner to that of Example 17-(1) to give 3-[2-(N-t-butoxycarbonylglycyl)hydrazino]-5-methyl-6-phenyl-1,2,4-triazine (4.068 g). The purification was conducted with column chromatography on silica gel (80 g) using a mixture of methylene chloride and methanol (30:1) as an eluent.

Workup

  1. customgave a solution

Sources & evidence

ORD record
ord-7ab2032db55548c48dce9b4e15b59520
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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