Potassium Carbonate → HCID 22099380, compound

HRID 1457576Notes

Reaction equation

HRID 1457576 reaction equation
[C:1]([O:5][C:6]([NH:8][NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[C:1]([O:5][C:6]([NH:8][NH:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 70091tert-Butyl carbazateHCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 22099380HCID 22099380, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25 g of tert-butoxycarbonyl hydrazine, 37 g of ethyl 6-bromohexanoate, 26 g of potassium carbonate and 40 ml of hexamethylphosphoramide (HMPA) was stirred at room temperature for 3.5 hours. Water was added to the mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed and dried, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=3:1) to give 16 g of ethyl 6-(N'-tert-butoxycarbonylhydrazino)hexanoate (state: oily product, IR: 3350, 1740, 1720 cm-1).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent; chloroform:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-cc74810860354325a5d2f73acb661d00
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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