Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → HCID 85472742, compound

HRID 2177187Notes

Reaction equation

HRID 2177187 reaction equation
[F:1][C:2]1([F:17])[CH2:5][CH:4]([C:6]2[C:10]([CH2:11][OH:12])=[C:9]([C:13]([F:16])([F:15])[F:14])[S:8][N:7]=2)[CH2:3]1.[F:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[CH:22]=[C:23]([F:26])[C:24]=1O>>[F:17][C:2]1([F:1])[CH2:5][CH:4]([C:6]2[C:10]([CH2:11][O:12][C:24]3[C:23]([F:26])=[CH:22][C:21]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:20][C:19]=3[F:18])=[C:9]([C:13]([F:15])([F:16])[F:14])[S:8][N:7]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90418237HCID 90418237, compound

Product 1

HCID 85472742HCID 85472742, compound

Procedure

The title compound was prepared according to the procedure described in Example 1 starting following Step 5 and 6 coupling (3-(3,3-difluorocyclobutyl)-5-(trifluoromethyl)isothiazol-4-yl)methanol and ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (300 MHz, CD3OD) δ 6.96 (d, J=7.2 Hz, 2H), 5.19 (s, 2H), 3.80-3.93 (m, 1H), 2.99-3.16 (m, 4H), 2.89 (t, J=7.5 Hz, 2H), 2.61 (t, J=7.2 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C18H14F7NO3S, 456.1 (M−H). found 456.1.

Workup

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

Sources & evidence

ORD record
ord-9638f84c129846d98f4c4c8c1e2ddb23
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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