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

HRID 75769

Reaction equation

HRID 75769 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:11]=[C:12]([C:16]4[CH:20]=[C:19]([C:21](O)=[O:22])[O:18][N:17]=4)[CH:13]=[CH:14][CH:15]=3)[S:8][C:4]=2[CH:3]=1.Cl.[CH3:27][O:28][C:29](=[O:35])[C@@H:30]([NH2:34])[CH2:31][O:32][CH3:33]>>[CH3:27][O:28][C:29](=[O:35])[C@@H:30]([NH:34][C:21]([C:19]1[O:18][N:17]=[C:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][C:7]3[S:8][C:4]4[CH:3]=[C:2]([F:1])[CH:25]=[CH:24][C:5]=4[N:6]=3)[CH:11]=2)[CH:20]=1)=[O:22])[CH2:31][O:32][CH3:33]

Participants

3

Reactant 2

HCID 13945137methyl (2S)-2-amino-3-methoxypropanoate hydrochlorideHCID 866564873-[3-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carboxylic acid

Product 1

HCID 46180820(S)-2-({3-[3-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carbonyl}-amino)-3-methoxy-propionic acid methyl esterYield 68%

Procedure

The title compound was prepared according to the procedure as set forth in Example 5, except that 3-[3-(6-fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carboxylic acid was used instead of the compound of Example 2 and (S)-2-amino-3-methoxy-propionic acid methyl ester hydrochloride was used instead of (S)-Val-OMe.HCl to yield 68% of the title compound. Mass (ES+): 471 (M++1), 493 (M++Na); IR (KBr): 3319, 2929, 1740, 1670, 1571, 1474; 1H NMR (DMSO-d6) δ: 3.29 (s, 3H), 3.67 (s, 3H), 3.74 (m, 2H), 4.74 (m, 1H), 7.18 (m, 1H), 7.53 (m, 2H), 7.62 (dd, 1H), 7.72 (s, 1H), 7.76 (dd, 1H), 7.95 (m, 1H), 8.32 (s, 1H), 9.39 (d, 1H), 10.70 (s, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-f413ef7cf1c94fb28a2f8f99856d7759
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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