1,2-Dichloroethane → Trifluoro-methanesulfonic acid 5-[3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionylamino]-5,6,7,8-tetrahydro-naphthalen-2-yl Ester

HRID 32106Notes

Reaction equation

HRID 32106 reaction equation
[C:1]1([CH:7]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)(=[O:15])=[O:14])[CH2:8][C:9](O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:26][CH:27]1[CH2:36][CH2:35][CH2:34][C:33]2[CH:32]=[C:31]([O:37][S:38]([C:41]([F:44])([F:43])[F:42])(=[O:40])=[O:39])[CH:30]=[CH:29][C:28]1=2.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[C:1]1([CH:7]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:23])[F:25])[CH:17]=2)(=[O:15])=[O:14])[CH2:8][C:9]([NH:26][CH:27]2[CH2:36][CH2:35][CH2:34][C:33]3[CH:32]=[C:31]([O:37][S:38]([C:41]([F:44])([F:42])[F:43])(=[O:40])=[O:39])[CH:30]=[CH:29][C:28]2=3)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 454390913-Phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionic acidHCID 59486419HCID 59486419, compound

Product 1

HCID 86598505Trifluoro-methanesulfonic acid 5-[3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionylamino]-5,6,7,8-tetrahydro-naphthalen-2-yl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionic acid (4.31 g, 11.56 mmol), trifluoro-methanesulfonic acid 5-amino-5,6,7,8-tetrahydro-naphthalen-2-yl ester (Step D, 3.10 g, 10.51 mmol), HOBt (Aldrich, 1.28 g, 9.46 mmol), and CH2Cl2 (30 mL) was added EDC (Aldrich, 3.02 g, 15.76 mmol). The reaction was stirred at RT overnight and diluted with CH2Cl2 (100 mL). The organic phase was washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by silica gel chromatography (16-30% EtOAc-hexane) to afford the title compound as an off-white solid. MS (ESI): 651 (M+H)+.

Workup

  1. washThe organic phase was washed with saturated NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by silica gel chromatography (16-30% EtOAc-hexane)

Sources & evidence

ORD record
ord-e2374bb8c7484fc196589113c5d3c3e8
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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