Hydrazine hydrate (1:1) → HCID 13622588, compound

HRID 280950Notes

Reaction equation

HRID 280950 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:25][C@@H:26]1[C:32](=[O:33])[N:31]([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:30]2[CH:42]=[CH:43][CH:44]=[CH:45][C:29]=2[O:28][CH2:27]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1C(=O)C2=CC=CC=C2[C:15]1=[O:24])=[O:5])[CH3:2].[OH2:46].NN>C(O)C>[C:38]([O:46][C:15]([NH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([NH:25][C@@H:26]1[C:32](=[O:33])[N:31]([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:30]2[CH:42]=[CH:43][CH:44]=[CH:45][C:29]=2[O:28][CH2:27]1)[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:24])([CH3:41])([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13622565HCID 13622565, compound

Product 1

HCID 13622588HCID 13622588, compoundYield 183.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 3(S)-[1(S)-ethoxycarbonyl-8-phthalimidooctyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.55 g), hydrazine hydrate (0.22 g) and ethanol (10 ml) is allowed to stand overnight at room temperature. After evaporation of ethanol, the residue is dissolved in water (50 ml) and extracted with ethyl acetate (50 ml×4). Water (50 ml) and sodium bicarbonate (0.6 g) are added to the organic extract, and to the resulting mixture is added dropwise di-tert-butyl dicarbonate (0.29 g) with stirring. After stirring for 30 minutes at room temperature, the ethyl acetate layer is separated, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography using hexane:ethyl acetate (2:1-1:1) as an eluent to give tert-butyl 3(S)-[8-tert-butoxycarbonylamino-1(S)-ethoxycarbonyloctyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.48 g) as a colorless oil.

Workup

  1. customAfter evaporation of ethanol
  2. dissolutionthe residue is dissolved in water (50 ml)
  3. extractionextracted with ethyl acetate (50 ml×4)
  4. additionWater (50 ml) and sodium bicarbonate (0.6 g) are added to the organic extract
  5. additionto the resulting mixture is added dropwise di-tert-butyl dicarbonate (0.29 g)
  6. stirringAfter stirring for 30 minutes at room temperature
  7. customthe ethyl acetate layer is separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8b692b9850ad4e3fbd0a126220d3bde3
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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