Hydrochloric Acid → HCID 178503694, compound

HRID 2121162Notes

Reaction equation

HRID 2121162 reaction equation
[ClH:1].C[O:3][C:4](=[O:35])[C@H:5]([CH2:31][CH2:32][S:33][CH3:34])[NH:6][C:7](=[O:30])[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:23])[C@H:15]([CH2:17][C:18]2[N:22]=[CH:21][NH:20][CH:19]=2)[NH2:16])=[CH:10][C:9]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O[Li].O.Cl>C1COCC1.O>[ClH:1].[NH2:16][C@H:15]([C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:7]([NH:6][C@H:5]([C:4]([OH:35])=[O:3])[CH2:31][CH2:32][S:33][CH3:34])=[O:30])=[C:9]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:10]=1)=[O:23])[CH2:17][C:18]1[N:22]=[CH:21][NH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 178501477HCID 178501477, compound

Product 1

HCID 178503694HCID 178503694, compoundYield 32%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of [4-(L-histidyl)-2-phenylbenzoyl methionine methyl ester hydrochloride (98.9 mg, 0.200 mmol), prepared as in Example 184B, in THF/H2O (4:1, 20 mL) was added LiOH.H2O (68.5 mg, 1.60 mmol). The solution was stirred for 6 hours and then was treated with 1 M aqueous HCl (20 mL). The mixture was lyopholized to provide a white solid. Recrystallization from methanol afforded [4-(L-histidyl)-2-phenylbenzoyl]methionine hydrochloride (31 mg, 32%) as a white solid. 1H NMR (D2O) δ 1.68-1.82 (m, 1H), 1.88-1.99 (comp, 2H), 2.02 (s, 3H), 2.00-2.12 (m, 1H), 3.28-3.32 (m, 2H), 3.49 (d, 2H), 4.28-4.34 (m, 1H), 4.44 (t, 1H), 7.36-7.53 (comp, 8H), 7.57 (m, 1H), 8.67 (m, 1H); LRMS (CI): 482 (M+1)+, 701.

Workup

  1. customto provide a white solid
  2. customRecrystallization from methanol

Sources & evidence

ORD record
ord-f34f88a4483545e1ab886dfed6e60d52
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

Loading…