Benzyl chloroformate → HCID 18790412, compound

HRID 1106970Notes

Reaction equation

HRID 1106970 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[OH-:12].[Na+].[C:14]([CH:17]([CH2:22][CH2:23][CH2:24][NH2:25])[CH2:18][CH2:19][CH2:20][NH2:21])([OH:16])=[O:15]>O>[CH2:5]([O:4][C:2]([NH:25][CH2:24][CH2:23][CH2:22][CH:17]([CH2:18][CH2:19][CH2:20][NH:21][C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:12])[C:14]([OH:16])=[O:15])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 131861655-Amino-2-(3-aminopropyl)pentanoic acid

Product 1

HCID 18790412HCID 18790412, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

24.48 g (143.5 mmol) of benzyl chloroformate and 5N aqueous sodium hydroxide solution are simultaneously added in drops at 0° C. to 10 g (57.39 mmol) of 4-carboxy-1,7-diaminoheptane (produced according to: A. Reissert, Chem. Ber. 26, 2137 (1893); 27, 979 (1894)) in 150 ml of water, and the pH is kept at 10. It is stirred overnight at room temperature. It is extracted twice with 150 ml of ethyl acetate each. The aqueous phase is carefully acidified with 4N aqueous hydrochloric acid (pH 2) and extracted three times with 200 ml of ethyl acetate each. The organic phase is dried on magnesium sulfate and evaporated to the dry state in a vacuum.

Workup

  1. customproduced
  2. extractionIt is extracted twice with 150 ml of ethyl acetate each
  3. extractionextracted three times with 200 ml of ethyl acetate each
  4. customThe organic phase is dried on magnesium sulfate
  5. customevaporated to the dry state in a vacuum

Sources & evidence

ORD record
ord-0b993bdacd9f419299b7f43dc133f546
Source dataset
uspto-grants-2000_05
Patent number
US06057419

Reaction notes

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