Hydrochloric Acid → HCID 86739491, compound

HRID 1262891Notes

Reaction equation

HRID 1262891 reaction equation
C([O:5]C([NH:8][C@H:9]([C:22]([NH:24][C@@H:25]([C:31]([NH:33][CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:32])[CH2:26][CH2:27][C:28]([NH2:30])=[O:29])=[O:23])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]C(C)(C)C)=[CH:13][CH:12]=1)=O)(C)(C)C.[ClH:43]>C(O)(=O)C>[OH2:5].[ClH:43].[NH2:8][C@H:9]([C:22]([NH:24][C@@H:25]([C:31]([NH:33][CH2:34][CH2:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:32])[CH2:26][CH2:27][C:28]([NH2:30])=[O:29])=[O:23])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86739492HCID 86739492, compound

Product 1

HCID 86739491HCID 86739491, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [N-(tert-butyloxycarbonyl)-O-(tert-butyl)-L-tyrosyl]-N1 -(3-phenylpropyl)-D-glutamamide (700 mg.) in acetic acid saturated with hydrogen chloride (15 ml.) was stirred at room temperature for one hour, then stripped of volatiles under vacuum at 40° C. An aqueous solution of the residue was filtered and lyophilized, affording as an amorphous white solid L-tyrosyl-N1 -(3-phenylpropyl)-D-glutamamide monohydrochloride hydrate (4:3) (545 mg.; [α]D25 +46.4°, c=1, methanol), whose free base is the compound of Formula II wherein Q is Gln, R1, R2 and R5 are each hydrogen and R4 is (CH2)nY wherein n is 3 and Y is phenyl.

Workup

  1. customstripped of volatiles under vacuum at 40° C
  2. filtrationAn aqueous solution of the residue was filtered

Sources & evidence

ORD record
ord-a422c8360b96457088152c63fbb50a38
Source dataset
uspto-grants-1984_06
Patent number
US04454120

Reaction notes

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