Ethanol → ethyl (2R)-2-amino-5-[(benzoyloxy)carbonyl]aminopentanoate hydrochloride

HRID 47774Notes

Reaction equation

HRID 47774 reaction equation
Cl.[NH2:2][C@H:3]([CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:4]([OH:6])=[O:5].S(Cl)([Cl:23])=[O:22].[CH2:25](O)[CH3:26]>>[ClH:23].[NH2:2][C@H:3]([CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:4]([O:6][CH2:25][CH3:26])=[O:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 69885572(2R)-2-amino-5-[(benzyloxy)carbonyl]aminopentanoic acid hydrochloride

Product 1

HCID 86584446ethyl (2R)-2-amino-5-[(benzoyloxy)carbonyl]aminopentanoate hydrochloride

Conditions

Temperature
20 °C

Procedure

A solution of 12.5 g of (2R)-2-amino-5-[(benzyloxy)carbonyl]aminopentanoic acid hydrochloride in 200 cm3 of ethanol is cooled to a temperature in the region of −20° C. 6.5 cm3 of thionyl chloride are added dropwise and the mixture is then stirred at a temperature in the region of 20° C. for 18 hours. The reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C. to give 13 g of ethyl (2R)-2-amino-5-[(benzoyloxy)carbonyl]aminopentanoate hydrochloride [mass spectrum: DCI m/z=295 MH+].

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C.

Sources & evidence

ORD record
ord-9ced4970efc84c1bb4b2ae7a1c24e74f
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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