Hydrochloric Acid → HCID 60202677, compound

HRID 1952658Notes

Reaction equation

HRID 1952658 reaction equation
C[O:2][C:3](=[O:37])[C@@H:4]([NH:17][C:18]([C:20]1[S:24][C:23]([NH:25][C:26](=[O:35])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)=[N:22][C:21]=1[CH3:36])=[O:19])[CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[CH:9]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[F:15][C:10]1[CH:9]=[C:8]([CH:13]=[C:12]([F:14])[CH:11]=1)[C:7]([NH:6][CH2:5][C@H:4]([NH:17][C:18]([C:20]1[S:24][C:23]([NH:25][C:26](=[O:35])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)=[N:22][C:21]=1[CH3:36])=[O:19])[C:3]([OH:37])=[O:2])=[O:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86671250HCID 86671250, compound

Product 1

HCID 60202677HCID 60202677, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of (S)-3-(3,5-Difluoro-benzoylamino)-2-({2-[2-(3-hydroxy-phenyl)-acetylamino]-4-methyl-thiazole-5-carbonyl}-amino)-propionic acid methyl ester (89.9 mg, 0.169 mmol) in THF (4 mL) and water (2 mL) was added lithium hydroxide monohydrate (80 mg, 1.91 mmol) The reaction was stirred at 25° C. for 1.5 h. The reaction mixture was acidified with concentrated HCl and concentrated under reduced pressure. The resulting crude compound was purified by HPLC to give (S)-3-(3,5-Difluoro-benzoylamino)-2-({2-[2-(3-hydroxy-phenyl)-acetylamino]-4-methyl-thiazole-5-carbonyl}-amino)-propionic acid (51.7 mg, 59%) as a white solid. MS m/e 519.5 (M+H+)

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting crude compound was purified by HPLC

Sources & evidence

ORD record
ord-87b6bf0f91e649c78f335f8e3c1678d2
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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