tert-Butyl carbazate → Tert-butyl 2-(4-(benzyloxy)benzoyl)hydrazinecarboxylate

HRID 606327Notes

Reaction equation

HRID 606327 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[NH:19][NH2:20].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.CO.C(Cl)Cl.CCN(CC)CC>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:20][NH:19][C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 70091tert-Butyl carbazateHCID 738804-(Benzyloxy)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 66822257Tert-butyl 2-(4-(benzyloxy)benzoyl)hydrazinecarboxylateYield 87%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-benzyloxybenzoic acid (0.780 g, 3.42 mmol), tert-butyl carbazate (0.443 g, 3.35 mmol), Et3N (0.5 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.05 g, 5.47 mmol) and 1-hydroxybenzotriazole hydrate (0.778 g, 5.76 mmol) in N,N-dimethylformamide (27 mL) was stirred at room temperature for 2 days. The reaction was concentrated and diluted in dichloromethane. The organic phase was washed twice with water, dried with MgSO4 and concentrated. The residue was purified on column chromatography (silica gel, 5% MeOH in CH2Cl2) and tert-butyl 2-[4-(benzyloxy)benzoyl]hydrazine carboxylate (0.998 g, yield: 85%) was identified by NMR spectroscopy.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted in dichloromethane
  3. washThe organic phase was washed twice with water
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c302365a8adb4403865138393f3596ac
Source dataset
uspto-grants-2011_03
Patent number
US07915295B2

Reaction notes

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