Trifluoroacetic acid → 3-(4-Carboxy-2-methoxyphenylmethylthio)-3-[2-(8-phenyloctyl)phenyl]propionic acid

HRID 1034317Notes

Reaction equation

HRID 1034317 reaction equation
O[CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][C:4]([O:6]C(C)(C)C)=[O:5].[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[CH2:42][SH:43])[C:36]([OH:38])=[O:37].FC(F)(F)C(O)=O>C(Cl)Cl>[C:36]([C:35]1[CH:39]=[CH:40][C:41]([CH2:42][S:43][CH:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:3][C:4]([OH:6])=[O:5])=[C:33]([O:32][CH3:31])[CH:34]=1)([OH:38])=[O:37]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 15617420Tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionateHCID 190238253-Methoxy-4-mercaptomethylbenzoic acid

Product 1

HCID 190237863-(4-Carboxy-2-methoxyphenylmethylthio)-3-[2-(8-phenyloctyl)phenyl]propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.54 g (1.32 mmol) of tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionate and 0.52 gm, (2.64 mmol) of 3-methoxy-4-mercaptomethylbenzoic acid in 10 ml of methylene chloride at 0° was treated dropwise with 20 ml of trifluoroacetic acid. Stirring was continued at 0° for 4 hours and 221 for 1 hour, and all the solvents were thoroughly evaporated. The residue was crystallized first from H2O/MECN (1:4), and then from Me2CO/hexane, and to yield the product, 0.26 gm. nmr (CDCl3 /Me2CO/DMSO): 7.05-7.72(m, 12H), 4.52 (d of d, 1H), 4.83(d, 1H), 4.82(s,3H), 4.68(d.1H), 2.88-3.24(m, 2H), 2.36-2.74 (m, 4H), 1.10-1.75(m,12H).

Workup

  1. wait221 for 1 hour
  2. customall the solvents were thoroughly evaporated
  3. customThe residue was crystallized first from H2O/MECN (1:4)
  4. customfrom Me2CO/hexane, and to yield the product, 0.26 gm

Sources & evidence

ORD record
ord-5447c5500cb64340ad53006e31361c76
Source dataset
uspto-grants-1994_05
Patent number
US05314918

Reaction notes

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