Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → HCID 90418136, compound

HRID 2177233Notes

Reaction equation

HRID 2177233 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=2)=[N:5][S:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.[OH:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[C:22]([CH3:33])[C:21]=1[CH3:34]>>[CH:8]1([C:7]2[S:6][N:5]=[C:4]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=3)[C:3]=2[CH2:2][O:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[C:22]([CH3:33])[C:21]=2[CH3:34])[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 90418638HCID 90418638, compound

Product 1

HCID 90418136HCID 90418136, compound

Procedure

The title compound was prepared according to the procedure described in Example 122 following Steps 5 and 7 by coupling of 4-(chloromethyl)-5-cyclopropyl-3-(4-ethylphenyl)-1,2-thiazole with ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate to afford the desired product as a yellow oil. 1H NMR (400 MHz, CD3OD) δ 7.59 (d, J=8.4 Hz, 2H), 7.28 (d, J=8.0 Hz, 2H), 6.97 (d, J=8.4 Hz, 1H), 6.77 (d, J=8.4 Hz, 1H), 5.06 (s, 2H), 2.92 (t, J=8.0 Hz, 2H), 2.70 (q, J=7.6, 15.6 Hz, 2H), 2.52 (t, J=7.2 Hz, 2H), 2.25-2.27 (m, 4H), 2.11 (s, 3H), 1.20-1.28 (m, 5H), 0.88-0.87 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C26H29NO3S, 436.2 (M+H). found 436.2.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-19f30201abf54975bf8dcdd44cca35ff
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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