L-Hydroxyproline → HCID 21906752, compound

HRID 1005833Notes

Reaction equation

HRID 1005833 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[CH:14][C:13]=3[C:24]([F:27])([F:26])[F:25])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.OC1CCNC1.[OH:34][C@H:35]1[CH2:39][NH:38][C@H:37]([C:40]([OH:42])=[O:41])[CH2:36]1>>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:19]=[CH:20][N:21]=[C:22]([N:38]5[CH2:39][CH:35]([OH:34])[CH2:36][CH:37]5[C:40]([OH:42])=[O:41])[CH:23]=4)=[CH:14][C:13]=3[C:24]([F:25])([F:26])[F:27])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 5810L-HydroxyprolineHCID 982104-HydroxypyrrolidineHCID 865858674-(4-(2,3-Dihydro-benzo(1,4)dioxin-6-ylsulfanyl)-3-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 21906752HCID 21906752, compound

Procedure

The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 118 (0.033 g, 0.0779 mmol) and 3-hydroxypyrrolidine with trans-4-hydroxy-L-proline. A yellow solid 131 was obtained (0.017 g, 33%). 1H-NMR (CDCl3, 400 MHz) δ 2.42-2.51 (m, 1H), 3.66-3.72 (m, 1H), 3.85-3.91 (m, 1H), 4.00-4.06 (m, 1H), 4.28-4.34 (m, 4H), 4.64-4.69 (m, 1H), 4.85-4.95 (m, 1H), 6.81 (s, 1H), 6.92-6.96 (m, 2H), 7.03 (dd, J=1.8 Hz, 8.4 Hz, 1H), 7.06-7.10 (m, 2H), 7.50 (d, J=8.4 Hz, 1H), 7.79 (s, 1H), 7.92-7.96 (m, 1H); MS (APCI) m/z 519 (M+H)+.

Sources & evidence

ORD record
ord-55fd6c9ee52c40bc8feb1eed34f10632
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

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