Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → HCID 90418408, compound

HRID 2177174Notes

Reaction equation

HRID 2177174 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13])(=O)=O.[F:21][C:22]1[CH:23]=[C:24]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[CH:25]=[C:26]([F:29])[C:27]=1O>>[CH:16]1([C:8]2[C:7]([CH2:6][O:5][C:27]3[C:26]([F:29])=[CH:25][C:24]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:23][C:22]=3[F:21])=[C:11]([C:12]([F:15])([F:14])[F:13])[S:10][N:9]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90418178HCID 90418178, compound

Product 1

HCID 90418408HCID 90418408, compound

Procedure

The title compound was prepared according to the procedure described in Example 1 starting following Step 5 and 6 coupling (3-cyclopentyl-5-(trifluoromethyl)isothiazol-4-yl)methyl methanesulfonate and ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (400 MHz, CD3OD) δ6.89-6.96 (m, 2H), 5.26 (s, 2H), 3.57 (m, 1H), 2.89 (t, J=7.6 Hz, 2H), 2.61 (t, J=7.6 Hz, 2H), 2.06-2.12 (m, 2H), 1.81-1.97 (m, 4H), 1.69-1.79 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C19H15F5NO3S, 436.1 (M+H). found 436.1.

Workup

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

Sources & evidence

ORD record
ord-f274380bd7124318bac38a4279d2fe78
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…