Hydrazine hydrate (1:1) → HCID 13622577, compound

HRID 980629Notes

Reaction equation

HRID 980629 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[S:28][CH2:27]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:18](=[O:19])C2=CC=CC=C2C1=O)=[O:5])[CH3:2].[OH2:46].NN>C(O)C>[C:38]([O:46][C:18]([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]([CH3:39])([CH3:41])[CH3:40])=[O:36])[C:30]2[CH:42]=[CH:43][CH:44]=[CH:45][C:29]=2[S:28][CH2:27]1)[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:19])([CH3:41])([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13622547HCID 13622547, compound

Product 1

HCID 13622577HCID 13622577, compoundYield 184.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 10 ml of ethanol is dissolved 0.9 g of tert-butyl 3(R)-[1(S)-ethoxycarbonyl-8-phthalimidooctyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate, and 0.35 g of hydrazine hydrate is added to the solution. After the mixture is left standing at room temperature overnight, the mixture is concentrated under reduced pressure, diluted with water and extracted four times with 50 ml of ethyl acetate. Water (50 ml) and 1.0 g of sodium bicarbonate are added to the ethyl acetate layer, and 0.46 g of di-tertbutyl dicarbonate is added to the resulting mixture with stirring. After the mixture is stirred at room temperature for 30 minutes, the ethyl acetate layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silicagel column chromatography (hexane:ethyl acetate=2:1) to give 0.79 g of tert-butyl 3(R)-[8-tert-butoxycarbonylamino-1(S)-ethoxycarbonyloctyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate as a colorless oil.

Workup

  1. additionis added to the solution
  2. waitAfter the mixture is left
  3. concentrationthe mixture is concentrated under reduced pressure
  4. additiondiluted with water
  5. extractionextracted four times with 50 ml of ethyl acetate
  6. additionWater (50 ml) and 1.0 g of sodium bicarbonate are added to the ethyl acetate layer, and 0.46 g of di-tertbutyl dicarbonate
  7. additionis added to the resulting mixture
  8. stirringAfter the mixture is stirred at room temperature for 30 minutes
  9. dry with materialthe ethyl acetate layer is dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue is purified by silicagel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-7febc30be9f94c0db394884aca324cf1
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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