(S)-2-({3-[4-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carbonyl}-amino)-3-hydroxyl-propionic acid methyl ester → (S)-2-({3-[4-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carbonyl}-amino)-3-hydroxy-propionic acid

HRID 75766Notes

Reaction equation

HRID 75766 reaction equation
C[O:2][C:3](=[O:32])[C@@H:4]([NH:7][C:8]([C:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[S:23][C:24]4[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:25]=4[N:26]=3)=[CH:17][CH:16]=2)[CH:11]=1)=[O:9])[CH2:5][OH:6]>[OH-].[Na+].CO>[F:31][C:29]1[CH:28]=[CH:27][C:25]2[N:26]=[C:22]([NH:21][C:18]3[CH:19]=[CH:20][C:15]([C:12]4[CH:11]=[C:10]([C:8]([NH:7][C@@H:4]([CH2:5][OH:6])[C:3]([OH:32])=[O:2])=[O:9])[O:14][N:13]=4)=[CH:16][CH:17]=3)[S:23][C:24]=2[CH:30]=1

Participants

4

Reactant 1

HCID 46181904(S)-2-({3-[4-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carbonyl}-amino)-3-hydroxyl-propionic acid methyl ester

Product 1

HCID 46181905(S)-2-({3-[4-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carbonyl}-amino)-3-hydroxy-propionic acidYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

(S)-2-({3-[4-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carbonyl}-amino)-3-hydroxyl-propionic acid methyl ester was hydrolyzed by IN NaOH in MeOH to obtain the title compound in 53% yield. Mass (ES−): 443 (M++1); IR (KBr): 3435 (br), 3306, 171718, 1683, 1609, 1590, 1571 (br), 1439; 1H NMR (DMSO-d6) δ: 3.83 (m, 2H), 4.47 (m, 1H), 7.20 (m, 1H), 7.66 (m, 1H), 7.73 (s, 1H), 7.78 (m, 1H), 7.94 (br, 4H), 8.95 (d, 1H), 10.89 (br, COOH).

Sources & evidence

ORD record
ord-98e810f9f1644215968e51300c46e24a
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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