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

HRID 75774Notes

Reaction equation

HRID 75774 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[C:20]([C:21]([OH:23])=O)=[C:19]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[O:18][N:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.Cl.[CH3:33][O:34][C:35](=[O:41])[C@@H:36]([NH2:40])[CH2:37][O:38][CH3:39].[K+].[Br-]>>[CH3:33][O:34][C:35](=[O:41])[C@@H:36]([NH:40][C:21]([C:20]1[C:16]([C:13]2[CH:12]=[CH:11][C:10]([NH:9][C:7]3[S:8][C:4]4[CH:3]=[C:2]([F:1])[CH:31]=[CH:30][C:5]=4[N:6]=3)=[CH:15][CH:14]=2)=[N:17][O:18][C:19]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:23])[CH2:37][O:38][CH3:39]

Participants

4

Reactant 3

HCID 253877Potassium BromideHCID 13945137methyl (2S)-2-amino-3-methoxypropanoate hydrochlorideHCID 86656488HCID 86656488, compound

Product 1

HCID 86656490(S)-2-({3-[4-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-5-phenyl-isoxazole-4-carbonyl}-amino)-3-methoxy-propionic acid methyl esterYield 69%

Procedure

The title compound was prepared from 3-[4-(6-fluoro-benzothiazol-2-ylamino)-phenyl]-5-phenyl-isoxazole-4-carboxylic acid and (S)-2-amino-3-methoxy-propionic acid methyl ester hydrochloride as set forth in Example 5 and was obtained in 69% yield. Mass (ES+): 547 (M++1); IR (KBr): 3342, 3270, 1718, 1648, 1605, 1542; 1H NMR (DMSO-d6) δ: 3.23 (s, 3H), 3.61-3.68 (br, 5H), 4.79 (m, 1H), 7.16 (m, 1H), 7.53-7.58 (m, 4H), 7.80-7.87 (m, 7H), 9.53 (d, 1H), 10.73 (s, 1H, NH).

Workup

  1. customwas obtained in 69% yield

Sources & evidence

ORD record
ord-12cf83b1946841ef8e032c879770bac2
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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