Hydrogen chloride-ethyl acetate → 2-[(4-{2-[[(5-chloro-1H-indol-2-yl)carbonyl](heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid

HRID 914444Notes

Reaction equation

HRID 914444 reaction equation
C([O:5][C:6](=[O:38])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([C:26]([C:28]2[NH:29][C:30]3[C:35]([CH:36]=2)=[CH:34][C:33]([Cl:37])=[CH:32][CH:31]=3)=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.Cl.C(OCC)(=O)C>C(O)=O>[Cl:37][C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([C:26]([N:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:17][CH2:16][C:14]1[N:15]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:38])=[O:5])[S:12][CH:13]=1)=[O:27])=[CH:36]2

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 597592162-[(4-{2-[[(5-chloro-1H-indol-2-yl)carbonyl](heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597593862-[(4-{2-[[(5-chloro-1H-indol-2-yl)carbonyl](heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acidYield 78.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

2-[(4-{2-[[(5-Chloro-1H-indol-2-yl)carbonyl](heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (270 mg) obtained in Example 312-1 was dissolved in formic acid (5 mL), 4N hydrochloric acid/ethyl acetate solution (5 mL) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and ether was added to the residue to give the title compound (192 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ether
  2. additionwas added to the residue

Sources & evidence

ORD record
ord-35334908f44a404aa8c6651337680fb4
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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