4-Hydroxypyrrolidine → 4-Hydroxy-1-(4-(4-(2-methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridin-2-yl)-pyrrolidine-2-carboxylic acid

HRID 1246853

Reaction equation

HRID 1246853 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.OC1CCNC1.[OH:33][C@H:34]1[CH2:38][NH:37][C@@H:36]([C:39]([OH:41])=[O:40])[CH2:35]1>>[OH:33][CH:34]1[CH2:38][N:37]([C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([S:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[O:21][CH3:22])=[C:10]([C:23]([F:25])([F:24])[F:26])[CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:36]([C:39]([OH:41])=[O:40])[CH2:35]1

Participants

4

Reactant 3

HCID 982104-HydroxypyrrolidineHCID 440014Cis-4-Hydroxy-D-ProlineHCID 219068092-Chloro-4-(4-(2-methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 219067544-Hydroxy-1-(4-(4-(2-methoxy-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyridin-2-yl)-pyrrolidine-2-carboxylic acid

Procedure

The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 96 (0.039 g, 0.0985 mmol) and 3-hydroxypyrrolidine with cis-4-hydroxy-D-proline. A yellow solid 109 was obtained (0.030 g, 63%). MS (APCI) m/z 491 (M+H)+.

Sources & evidence

ORD record
ord-d45a6f114c204fc8898af7e59709e05f
Source dataset
uspto-grants-2006_10
Patent number
US07129247B2

Linked notes

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