Hydrazine hydrate (1:1) → HCID 13622586, compound

HRID 280941Notes

Reaction equation

HRID 280941 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:24][C@@H:25]1[C:31](=[O:32])[N:30]([CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:29]2[CH:41]=[CH:42][CH:43]=[CH:44][C:28]=2[O:27][CH2:26]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1C(=O)C2=CC=CC=C2[C:14]1=[O:23])=[O:5])[CH3:2].[OH2:45].NN>C(O)C>[C:37]([O:45][C:14]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([NH:24][C@@H:25]1[C:31](=[O:32])[N:30]([CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:38])[CH3:39])=[O:35])[C:29]2[CH:41]=[CH:42][CH:43]=[CH:44][C:28]=2[O:27][CH2:26]1)[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:23])([CH3:40])([CH3:39])[CH3:38]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13622562HCID 13622562, compound

Product 1

HCID 13622586HCID 13622586, compoundYield 153.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 10 ml of ethanol is dissolved 0.7 g of tert-butyl 3(S)-[1(S)-ethoxycarbonyl-7-phthalimidoheptyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate obtained in Example 64, and hydrazine hydrate (0.29 g) is added to the solution. After standing overnight, the solution is concentrated under reduced pressure, diluted with 50 ml of water and extracted five times with 30 ml each of ethyl acetate. To the ethyl acetate layer are added 50 ml of water and 0.7 g of sodium bicarbonate and 0.38 g of di-tert-butyl dicarbonate is added dropwise to the resulting mixture with stirring. After the mixture is stirring at room temperature for 0.5 hour, the ethyl acetate layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 0.51 g of tert-butyl 3(S)-[7-tert-butoxycarbonylamino-1(S)-ethoxycarbonylheptyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate as a colorless oil.

Workup

  1. additionis added to the solution
  2. concentrationthe solution is concentrated under reduced pressure
  3. additiondiluted with 50 ml of water
  4. extractionextracted five times with 30 ml each of ethyl acetate
  5. additionTo the ethyl acetate layer are added 50 ml of water and 0.7 g of sodium bicarbonate and 0.38 g of di-tert-butyl dicarbonate
  6. additionis added dropwise to the resulting mixture
  7. stirringAfter the mixture is stirring at room temperature for 0.5 hour
  8. dry with materialthe ethyl acetate layer is dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5dad5657c3934403a73fe843412589d9
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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