Ethyl 2,2-dimethyl-3-(4-sulfanylphenyl)propanoate → HCID 11653483, compound

HRID 2355786Notes

Reaction equation

HRID 2355786 reaction equation
C(OC(=O)C(C)(C)CC1C=CC(S)=CC=1)C.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([OH:39])([CH3:38])[C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=1)(=[O:26])=[O:25]>>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([C:27]1[CH:32]=[CH:31][C:30]([C@@:33]([OH:39])([CH3:38])[C:34]([F:36])([F:37])[F:35])=[CH:29][CH:28]=1)(=[O:26])=[O:25]

Participants

3

Reactant 2

HCID 4114055Ethyl 2,2-dimethyl-3-(4-sulfanylphenyl)propanoateHCID 52941171HCID 52941171, compound

Product 1

HCID 11653483HCID 11653483, compound

Procedure

Using the methods described above in Example 12, but substituting 2-chlorobenzenethiol for 3-(4-mercaptophenyl)-2,2-dimethylpropionic acid ethyl ester in step a, 2-[4-(2-chlorobenzenesulfonyl)phenyl]-1,1,1-trifluoropropan-2-ol was prepared. 1H NMR (CDCl3, 400 MHz) δ 8.27 (dd, J=2.0 Hz, 7.6 Hz, 1H), 7.98 (d, J=8.6 Hz, 2H), 7.75 (d, J=8.4 Hz, 2H), 7.57-7.44 (m, 3H), 2.61 (s, 1H), 1.80 (s, 3H). The racemic product was resolved by chiral HPLC. The flow rate was 20 mL/min on a Chiralcel OD-H 20 mm i.d.×250 mm, 5μ column (Daciel chemical Industries LTD), using isopropyl alcohol/hexanes (10/90) as the eluent.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-c5edc4093c08453ca4090491d92cef63
Source dataset
uspto-grants-2010_07
Patent number
US07754890B2

Reaction notes

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