Hydrochloric Acid → N-Acetyl-tyrosinyl-valinyl-(4-phenoxy)proline

HRID 2229928Notes

Reaction equation

HRID 2229928 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:40])[C@@H:6]1[CH2:10][CH:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][N:7]1[C:18](=[O:39])[C@H:19]([CH:36]([CH3:38])[CH3:37])[NH:20][C:21](=[O:35])[C@H:22]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[NH:23][C:24](=[O:26])[CH3:25].Cl>O1CCCC1.O>[C:24]([NH:23][C@H:22]([C:21]([NH:20][C@H:19]([C:18]([N:7]1[CH2:8][CH:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][C@H:6]1[C:5]([OH:40])=[O:4])=[O:39])[CH:36]([CH3:38])[CH3:37])=[O:35])[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 54377655N-Acetyl-tyrosinyl-valinyl-(4-phenoxy)proline Methyl Ester

Product 1

HCID 54232766N-Acetyl-tyrosinyl-valinyl-(4-phenoxy)prolineYield 49.9%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (57 mg, 1.37 mmol) was added to a solution of N-Acetyl-tyrosinyl-valinyl-(4-phenoxy)proline methyl ester (360 mg, 0.685 mmol) dissolved in 8 ml of tetrahydrofuran/water (1:1) and stirred at room temperature for 1 hour. The mixture was acidified with 10% hydrochloric acid giving a white precipitate that was collected to give 175 mg of the title compound.

Workup

  1. customwas collected

Sources & evidence

ORD record
ord-8b9ccbdcb00a430cbdc28721602966d7
Source dataset
uspto-grants-2002_07
Patent number
US06420522B1

Reaction notes

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