1-Hydroxybenzotriazole → Ethyl [2-({[tert-butyl(diphenyl)silyl]oxy}acetyl)hydrazino](oxo)acetate

HRID 1881929Notes

Reaction equation

HRID 1881929 reaction equation
[NH:1]([C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[NH2:2].[Si:10]([O:27][CH2:28][C:29](O)=[O:30])([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(#N)C.C(OCC)(=O)C.C(N(CC)CC)C>[Si:10]([O:27][CH2:28][C:29]([NH:2][NH:1][C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:30])([C:23]([CH3:25])([CH3:26])[CH3:24])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2786935Ethyl 2-hydrazinyl-2-oxoacetateHCID 111415642-((tert-Butyldiphenylsilyl)oxy)acetic acid

Product 1

HCID 59331270Ethyl [2-({[tert-butyl(diphenyl)silyl]oxy}acetyl)hydrazino](oxo)acetateYield 30.3%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl hydrazino(oxo)acetate (3.58 g) in acetonitrile (100 mL) were successively added triethylamine (6.86 mL), {[tert-butyl(diphenyl)silyl]oxy}acetic acid (7.74 g), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (5.20 g) and 1-hydroxybenzotriazole (415 mg) under ice-cooling. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with water and saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (3.20 g, yield 30%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. temperaturecooling
  2. washwashed with water and saturated aqueous sodium hydrogen carbonate
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f81bd77762e7496785d175a139d9a3ec
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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