1,1-Dichloroethane → HCID 72303602, compound

HRID 1747077Notes

Reaction equation

HRID 1747077 reaction equation
C([O:5][C:6](=[O:50])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][NH:17][C:18]([CH:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23](=[O:30])[N:22]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]3[NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:21]2[C:42]2[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][C:43]=2[Cl:49])=[O:19])[CH:10]=1)(C)(C)C.ClC(Cl)C.FC(F)(F)C(O)=O>>[Cl:49][C:43]1[CH:44]=[C:45]([Cl:48])[CH:46]=[CH:47][C:42]=1[CH:21]1[CH:20]([C:18]([NH:17][O:16][CH2:15][C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[O:8][CH2:7][C:6]([OH:50])=[O:5])=[O:19])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](=[O:30])[N:22]1[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]1[NH:37][S:38]([CH3:41])(=[O:40])=[O:39]

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 6422Trifluoroacetic acidHCID 72303221HCID 72303221, compound

Product 1

HCID 72303602HCID 72303602, compoundYield 27.3%

Procedure

A mixture of 730 mg of tert-butyl(3-{[({[(3RS,4RS)-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl]carbonyl}amino)oxy]methyl}phenoxy)acetate, 5 ml of dichloroethane, and 5 ml of trifluoroacetic acid was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent:chloroform-methanol). The crude purified product thus obtained was recrystallized from ethyl acetate to obtain 184 mg of (3-{[({[(3RS,4RS)-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl]carbonyl}amino)oxy]methyl}phenoxy)acetic acid as a colorless crystal.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (eluent:chloroform-methanol)
  3. customThe crude purified product
  4. customthus obtained
  5. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-beb07f0c56dc47eb82b4665418bba6df
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

Loading…