Hydrazine hydrate (1:1) → HCID 13622584, compound

HRID 280946Notes

Reaction equation

HRID 280946 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:23][C@@H:24]1[C:30](=[O:31])[N:29]([CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:28]2[CH:40]=[CH:41][CH:42]=[CH:43][C:27]=2[O:26][CH2:25]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1C(=O)C2=CC=CC=C2[C:13]1=[O:22])=[O:5])[CH3:2].[OH2:44].NN>C(O)C>[C:36]([O:44][C:13]([NH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([NH:23][C@@H:24]1[C:30](=[O:31])[N:29]([CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])[C:28]2[CH:40]=[CH:41][CH:42]=[CH:43][C:27]=2[O:26][CH2:25]1)[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:22])([CH3:39])([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13622559HCID 13622559, compound

Product 1

HCID 13622584HCID 13622584, compoundYield 175%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 3(S)-[1(S)-ethoxycarbonyl-6-phthalimidohexyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.65 g), hydrazine hydrate (0.27 g) and ethanol (10 ml) is allowed to stand overnight at room temperature. The mixture is concentrated in vacuo, diluted with water (50 ml) and extracted with ethyl acetate (50 ml×4). To a mixture of the organic extract, water (50 ml) and sodium bicarbonate (0.65 g) are added dropwise di-tert-butyl dicarbonate (0.36 g) with stirring at room temperature. After stirring for 30 minutes, the ethyl acetate layer is separated, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is subjected to silica gel column chromatography using hexane:ethyl acetate (2:1-1:1) as an eluent to yield tert-butyl 3(S)-[6-tert-butoxycarbonylamino-1(S)-ethoxycarbonylhexyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.54 g) as a colorless oil.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. additiondiluted with water (50 ml)
  3. extractionextracted with ethyl acetate (50 ml×4)
  4. additionTo a mixture of the organic extract, water (50 ml) and sodium bicarbonate (0.65 g)
  5. additionare added dropwise di-tert-butyl dicarbonate (0.36 g)
  6. stirringAfter stirring for 30 minutes
  7. customthe ethyl acetate layer is separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e81b81b301864fd7af645e53117bfa07
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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