Hydrochloric Acid → (S)-2-{[2-(2-1H-Indazol-4-yl-acetylamino)-4-methyl-thiazole-5-carbonyl]-amino}-3-[(thiophene-2-carbonyl)-amino]-propionic acid

HRID 1952659Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of the (S)-2-{[2-(2-1H-Indazol-4-yl-acetylamino)-4-methyl-thiazole-5-carbonyl]-amino}-3-[(thiophene-2-carbonyl)-amino]-propionic acid methyl ester (34 mg, 0.0646 mmol), lithium hydroxide monohydrate (32 mg, 0.763 mmol), THF (2 mL) and water (1 mL) was stirred at 25° C. for 1½ h. Aqueous 2N HCl was added and the reaction mixture was stirred for 2 hrs and then concentrated under reduced pressure. The resulting crude product was purified by HPLC to give (S)-2-{[2-(2-1H-Indazol-4-yl-acetylamino)-4-methyl-thiazole-5-carbonyl]-amino}-3-[(thiophene-2-carbonyl)-amino]-propionic acid (21 mg, 63.5%) as a white solid. MS m/e 513.5 (M+H+).

Workup

stirringthe reaction mixture was stirred for 2 hrs
concentrationconcentrated under reduced pressure
customThe resulting crude product was purified by HPLC

Sources & evidence

ORD record: ord-7a1b2f81b8f34000b0ae280a801b2943
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404859B2

Reaction notes

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