2-(3-Tert-butyl-5-methoxycarbonyl-benzyl)-2-[3-[(triphenyl-methyl)thio]propyl]malonic acid → 2-(3-Tert-butyl-5-methoxycarbonyl-benzyl)-5-[(triphenylmethyl)thio]-pentanoic acid

HRID 1352819Notes

Reaction equation

HRID 1352819 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:39]=[C:40]([C:42]([O:44][CH3:45])=[O:43])[CH:41]=1)[CH2:8][C:9]([CH2:16][CH2:17][CH2:18][S:19][C:20]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(C(O)=O)[C:10]([OH:12])=[O:11])([CH3:4])([CH3:3])[CH3:2]>CS(C)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:39]=[C:40]([C:42]([O:44][CH3:45])=[O:43])[CH:41]=1)[CH2:8][CH:9]([CH2:16][CH2:17][CH2:18][S:19][C:20]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([OH:12])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 121446622-(3-Tert-butyl-5-methoxycarbonyl-benzyl)-2-[3-[(triphenyl-methyl)thio]propyl]malonic acid

Product 1

HCID 121446632-(3-Tert-butyl-5-methoxycarbonyl-benzyl)-5-[(triphenylmethyl)thio]-pentanoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-(3-tert-butyl-5-methoxycarbonyl-benzyl)-2-[3-[(triphenylmethyl)thio]propyl]-malonic acid XI (6.71 g, 11 mmol) in DMSO (10 ml) was stirred at 130° C. for 1.5 hours. The solvent was removed under reduced pressure and water was added to the residual oil. The precipitate was filtered off, washed with water, and dried under vacuum to afford 2-(3-tert-butyl-5-methoxycarbonyl-benzyl)-5-[(triphenylmethyl)thio]-pentanoic acid XII (5.86 g, 10.3 mmol, 94%) as a white solid: 1H NMR (CD3OD) δ1.3 (s, 9H), 1.3-1.5 (m, 4H), 2.1 (m, 2H), 2.4 (m, 1H), 2.7 (m, 1H), 2.8 (m, 1H), 7.1-7.4 (m, 16H), 7.7 (s, 1H), 7.9 (s, 1H); 13C NMR (CD3OD) δ27.4, 31.7 (3C), 32.3, 32.7, 35.6, 39.2, 48.4, 67.7, 125.7, 127.7, 128.6, 128.9, 130.8, 131.6, 132.0, 140.8, 146.3, 152.7, 170.3, 178.8.

Workup

  1. customThe solvent was removed under reduced pressure and water
  2. additionwas added to the residual oil
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2213ec46ff3f418a8d2ae1dc7bcba9df
Source dataset
uspto-grants-2007_05
Patent number
US07220780B2

Reaction notes

Loading…