Benzyl chloroformate → HCID 53808165, compound

HRID 1382925Notes

Reaction equation

HRID 1382925 reaction equation
Cl.[NH2:2][C@@H:3]([CH3:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].[OH-].[Na+].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>O>[CH2:18]([O:17][C:15]([NH:2][C@@H:3]([CH3:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 86742774HCID 86742774, compound

Product 1

HCID 53808165HCID 53808165, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 g (166 mmol) of (S)-6-aminoheptanoic acid hydrochloride in 57 ml of water are added 57 ml of 4N aqueous sodium hydroxide solution and thereafter dropwise simultaneously at 10° 92 ml of 4N aqueous sodium hydroxide solution and 42 ml (294 mol) of benzyl chloroformate so that the pH value always lies between 10 and 12. After the precipitation of the product the mixture is stirred at 0° for a further 2 hours. Thereafter, 300 ml of water are added and the reaction mixture is extracted with ether. The aqueous phase is then acidified with 20 ml of concentrated hydrochloric acid and extracted with methylene chloride. The methylene chloride phase is dried over magnesium sulphate and evaporated. The crystals obtained are recrystallized from chloroform/hexane, whereby there are obtained 33.1 g (72%) of (S)-6-[1-(benzyloxy)formamido]heptanoic acid, m.p. 82°-83°.

Workup

  1. customAfter the precipitation of the product the mixture
  2. additionThereafter, 300 ml of water are added
  3. extractionthe reaction mixture is extracted with ether
  4. extractionextracted with methylene chloride
  5. dry with materialThe methylene chloride phase is dried over magnesium sulphate
  6. customevaporated
  7. customThe crystals obtained
  8. customare recrystallized from chloroform/hexane, whereby there

Sources & evidence

ORD record
ord-bd7b379665494afca5f79009549b18fc
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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