tert-Butyl carbazate → N'-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoyl}-hydrazinecarboxylic Acid Tert-Butyl Ester

HRID 349438Notes

Reaction equation

HRID 349438 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17](O)=[O:18])=[N:11][CH:10]=2)=[CH:5][CH:4]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:45]([O:49][C:50]([NH:52][NH2:53])=[O:51])([CH3:48])([CH3:47])[CH3:46]>CN(C)C=O.O>[C:45]([O:49][C:50]([NH:52][NH:53][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[C:14]([C:12]2[O:13][C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[CH:10][N:11]=2)[CH:15]=1)=[O:51])([CH3:48])([CH3:47])[CH3:46]

Participants

7

Reactant 4

HCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 588048453-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoic Acid

Product 1

HCID 58804849N'-{3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoyl}-hydrazinecarboxylic Acid Tert-Butyl EsterYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.5 g (5.0 mmol) of 3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoic acid from Preparation 4, 1.3 g (6.6 mmol) EDAC.HCl, 0.89 g (6.6 mmol) HOBT, and 0.87 g (6.6 mmol) hydrazinecarboxylic acid tert-butyl ester was dissolved in 20 mL of dimethylformamide. Stirring was continued 48 hours at room temperature. Water (60 mL) was added, and the product was extracted with 1:1 THF/EtOAc (2×). Combined the organic extracts and washed with saturated aqueous NaCl solution (3×), dried (MgSO4). Dried in a vacuum oven overnight at 70° C. to provide 1.6 g (82%) of desired product. MS: m/z (APCI, AP+) 410 [M−]+

Workup

  1. extractionthe product was extracted with 1:1 THF/EtOAc (2×)
  2. washwashed with saturated aqueous NaCl solution (3×)
  3. dry with materialdried (MgSO4)
  4. customDried in a vacuum oven overnight at 70° C.

Sources & evidence

ORD record
ord-b47bd698ea0c4198ab4cc4700c5be6f9
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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