4-Hydroxybenzophenone → HCID 58822573, compound

HRID 459116Notes

Reaction equation

HRID 459116 reaction equation
C([O:3][C:4](=[O:23])[C@@H:5]([O:21][CH3:22])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)C.O[C:25]1[CH:38]=[CH:37][C:28]([C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:30])=[CH:27][CH:26]=1>C1COCC1>[C:29]([C:31]1[CH:36]=[CH:35][C:34]([O:20][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([C:10]3[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:21][CH3:22])[C:4]([OH:3])=[O:23])=[CH:12][CH:11]=3)=[CH:14][CH:15]=2)=[CH:33][CH:32]=1)(=[O:30])[C:28]1[CH:37]=[CH:38][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 143474-HydroxybenzophenoneHCID 58822846HCID 58822846, compound

Product 1

HCID 58822573HCID 58822573, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S)-3-(4′-Hydroxymethyl-biphenyl-4-yl)-2-methoxy-propionic acid ethyl ester from Step A, was treated with 4-hydroxybenzophenone under the standard Mitsunobu coupling procedure B (THF). The product obtained after chromatography was hydrolyzed using the Standard Procedure C to get the title compound. 1H-NMR (CDCl3, 200.15 MHz): 7.86–7.73 (m, 4H), 7.63–7.43 (m, 9H), 7.34–7.29 (m, 2H), 7.05 (d, 2H, J=9.1), 5.18 (s, 2H), 4.06 (dd, 1H, J=7.3, 4.0), 3.42 (s, 3H), 3.20 (dd, 1H, J=14.5, 4.0), 3.06 (dd, 1H, J=14.5, 7.3). MS (ES) for C30H26O5 [M+H]+: 467.2, [M+Na]+: 489.2.

Workup

  1. customThe product obtained after chromatography

Sources & evidence

ORD record
ord-4a28ad987c9544d898452bf26aa38ea9
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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