Hydrazine hydrate (1:1) → HCID 13622590, compound

HRID 280955Notes

Reaction equation

HRID 280955 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:26][C@@H:27]1[C:33](=[O:34])[N:32]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:31]2[CH:43]=[CH:44][CH:45]=[CH:46][C:30]=2[O:29][CH2:28]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])C2=CC=CC=C2C1=O)=[O:5])[CH3:2].[OH2:47].NN>C(O)C>[C:39]([O:20][C:19]([NH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([NH:26][C@@H:27]1[C:33](=[O:34])[N:32]([CH2:35][C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])[C:31]2[CH:43]=[CH:44][CH:45]=[CH:46][C:30]=2[O:29][CH2:28]1)[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:47])([CH3:42])([CH3:41])[CH3:40]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13622568HCID 13622568, compound

Product 1

HCID 13622590HCID 13622590, compoundYield 159.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 3(S)-[1(S)-ethoxycarbonyl-9-phthalimidononyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.46 g), hydrazine hydrate (0.18 g) and ethanol (10 ml) is allowed to stand overnight at room temperature. The mixture is concentrated under reduced pressure, diluted with water (50 ml) and extracted with ethyl acetate (50 ml×4). Water (50 ml) and sodium bicarbonate (0.5 g) are added to the organic extract, and to the resulting mixture is added dropwise di-tert-butyl dicarbonate (0.24 g) with stirring. After stirring for 30 minutes at room temperature, the ethyl acetate layer is dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography using hexane-ethyl acetate (2:1) as an eluent to yield tert-butyl 3(S)-[9-tert-butoxycarbonylamino-1(S)-ethoxycarbonylnonyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.35 g) as a colorless oil.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. additiondiluted with water (50 ml)
  3. extractionextracted with ethyl acetate (50 ml×4)
  4. additionWater (50 ml) and sodium bicarbonate (0.5 g) are added to the organic extract
  5. additionto the resulting mixture is added dropwise di-tert-butyl dicarbonate (0.24 g)
  6. stirringAfter stirring for 30 minutes at room temperature
  7. dry with materialthe ethyl acetate layer is dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3aa3b42c1875482bae8e4068e99e4c65
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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