Hydrazinecarboxylic acid, ethyl ester → HCID 86704546, compound

HRID 633459Notes

Reaction equation

HRID 633459 reaction equation
[Si:1]([O:8][CH2:9][C:10]1([CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[O:15][C:14]2[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:13]=2[NH:12][C:11]1=S)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[NH2:34]>C(O)C>[Si:1]([O:8][CH2:9][C:10]1([CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[O:15][C:14]2[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:13]=2[N:12]=[C:11]1[NH:34][NH:33][C:35]([O:37][CH2:38][CH3:39])=[O:36])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 86704545HCID 86704545, compound

Product 1

HCID 86704546HCID 86704546, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,2-Bis(((tert-butyldimethylsilyl)oxy)methyl)-6-nitro-2H-benzo[b][1,4]oxazine-3(4H)-thione (4.6 g) and ethyl hydrazinecarboxylate (2.88 g, 3.0 eq.) were suspended in ethanol (50 ml). The reaction mixture was refluxed for three days. The mixture was then evaporated. The residue was purified by Combiflash chromatography (EtOAc in hexanes=0-80%) to give ethyl 2-(2,2-bis(((tert-butyldimethylsilyl)oxy)methyl)-6-nitro-2H-benzo[b][1,4]oxazin-3-yl)hydrazine-1-carboxylate (4 g).

Workup

  1. temperatureThe reaction mixture was refluxed for three days
  2. customThe mixture was then evaporated
  3. customThe residue was purified by Combiflash chromatography (EtOAc in hexanes=0-80%)

Sources & evidence

ORD record
ord-9b031ed02aba4e28b85bbd7b2a46abad
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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