Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → HCID 90418664, compound

HRID 2177164Notes

Reaction equation

HRID 2177164 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([F:24])[CH:17]=2)=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13])(=O)=O.O[C:26]1[C:31]([F:32])=[CH:30][C:29]([CH2:33][CH2:34][C:35]([O:37]CC)=[O:36])=[CH:28][C:27]=1[F:40]>>[F:32][C:31]1[CH:30]=[C:29]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH:28]=[C:27]([F:40])[C:26]=1[O:5][CH2:6][C:7]1[C:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([F:24])[CH:17]=2)=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13]

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90418146HCID 90418146, compound

Product 1

HCID 90418664HCID 90418664, compound

Procedure

The title compound was prepared according to the procedure described in Example 1 starting following Step 5 and 6 coupling (3-(3-fluoro-4-methoxyphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methyl methanesulfonate and ethyl 3-(4-hydroxy-3,5-difluorophenyl)propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (400 MHz, CD3OD) δ 7.55-7.63 (m, 2H), 7.22 (t, J=8.8 Hz, 2H), 6.86-6.91 (m, 2H), 5.22 (s, 2H), 3.97 (s, 3H), 2.88 (t, J=7.2 Hz, 2H), 2.60 (t, J=7.5 Hz, 2H). Mass spectrum (ESI, m/z): Calcd. for C21H15F6NO4S, 490.1 (M−H). found 489.9.

Workup

  1. customThe title compound was prepared
  2. customfollowed by hydrolysis

Sources & evidence

ORD record
ord-391dd67bbbca4e8798e0b44b3fbfb20c
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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