(R)-(-)-2-Amino-1-phenylethanol → (R)-N-(2-hydroxy-2-phenylethyl)-4-methyl-2-(2-oxo-3-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)thiazole-5-carboxamide

HRID 2067434Notes

Reaction equation

HRID 2067434 reaction equation
C(N1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)C1C=CC=CC=1.[CH3:23][C:24]1[N:25]=[C:26]([N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][C:45]([F:48])([F:47])[F:46])=[CH:40][CH:39]=3)[C:33]2=[O:49])[S:27][C:28]=1[C:29](O)=[O:30].[NH2:50][CH2:51][C@@H:52]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[OH:53]>>[OH:53][C@H:52]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH2:51][NH:50][C:29]([C:28]1[S:27][C:26]([N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][C:45]([F:47])([F:46])[F:48])=[CH:40][CH:39]=3)[C:33]2=[O:49])=[N:25][C:24]=1[CH3:23])=[O:30]

Participants

4

Reactant 3

HCID 6951165(R)-(-)-2-Amino-1-phenylethanolHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 594812844-Methyl-2-(2-oxo-3-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid

Product 1

HCID 59481306(R)-N-(2-hydroxy-2-phenylethyl)-4-methyl-2-(2-oxo-3-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)thiazole-5-carboxamideYield 67%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 4-methyl-2-(2-oxo-3-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid to react with (R)-(−)-2-amino-1-phenylethanol, the title compound was obtained as a white powder in 67% yield: mp 149-151° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.38-7.16 (m, 9H), 6.24 (br s, 1H), 4.92-4.89 (m, 1H), 4.44 (s, 2H), 4.28-4.02 (m, 2H), 3.85-3.41 (m, 2H), 3.57-3.38 (m, 3H), 2.54 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 163.6, 157.5, 155.4, 152.8, 148.9, 141.7, 134.3, 129.7, 128.5, 127.8, 125.8, 121.4, 117.6, 73.5, 47.8, 47.2, 42.0, 41.7, 17.1; MS (ES+) m/z 521.3 (M+1).

Sources & evidence

ORD record
ord-9921e087dd8b49f9aa06ea7f8d4e878f
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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