Hydrochloric Acid → D-Isoglutamine benzyl ester hydrochloride

HRID 2082671Notes

Reaction equation

HRID 2082671 reaction equation
C(OC([NH:8][C@@H:9]([C:22](=[O:24])[NH2:23])[CH2:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=O)(C)(C)C.[ClH:25].CCOCC>C(OCC)(=O)C>[ClH:25].[NH2:8][C@@H:9]([C:22](=[O:24])[NH2:23])[CH2:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7037012tert-Butyloxycarbonyl-D-isoglutamine benzyl ester

Product 1

HCID 22802678D-Isoglutamine benzyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 3.36 of benzyl t-butyloxycarbonyl-D-isoglutaminate (4, n = 2) there is added 50 ml of a saturated solution of hydrogen chloride in ethyl acetate. The reaction mixture is stored at 22° C for 10 minutes and then 75 ml of ether is added to precipitate the product, which is collected by centrifugation and carefully dried in vacuo to give benzyl D-isoglutaminate hydrochloride (5, n = 2) which is used without further purification in step B of this example.

Workup

  1. customto precipitate the product, which
  2. customis collected by centrifugation
  3. customcarefully dried in vacuo

Sources & evidence

ORD record
ord-80a7360e696f4e5f8c8485480408c6f3
Source dataset
uspto-grants-1978_04
Patent number
US04082736

Reaction notes

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