Hydrazine hydrate (1:1) → HCID 86727348, compound

HRID 518993Notes

Reaction equation

HRID 518993 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[CH:15][C:16]3[O:21][CH2:20][C:19](=S)[N:18]([CH:23]([C:25](OCC)=[O:26])[CH3:24])[C:17]=3[CH:30]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:32][NH2:33]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([O:12][C:13]2[CH:30]=[C:17]3[C:16](=[CH:15][CH:14]=2)[O:21][CH2:20][C:19]2[N:18]3[CH:23]([CH3:24])[C:25](=[O:26])[NH:32][N:33]=2)[CH2:11]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86727347HCID 86727347, compound

Product 1

HCID 86727348HCID 86727348, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[4-(1-ethoxycarbonyl-ethyl)-3-thioxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxy]-azetidine-1-carboxylic acid tert-butyl ester (0.530 g, 1.22 mmol) in EtOH (10 mL) was added hydrazine hydrate (0.486 g, 9.72 mmol) and the mixture was heated at reflux for 2 h. The reaction mixture was cooled to ambient temperature, concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 20% EtOAc in petroleum ether) to give 3-(4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester (0.234 g, 52%) as a white solid. LC/MS (Table 1, Method 3) Rt=1.332 min.; MS m/z: 389 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by column chromatography on silica gel (eluting with 20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-4193f8ccbe0f43158656335a175a8efb
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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