Hydrochloric Acid → HCID 59192540, compound

HRID 1696890Notes

Reaction equation

HRID 1696890 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C@@H:14]([N:19]([S:21]([C:24]3[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26](F)[CH:25]=3)(=[O:23])=[O:22])[CH3:20])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([SH:43])=[CH:39][CH:38]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[C:1]([O:5][C:6](=[O:35])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C@@H:14]([N:19]([S:21]([C:24]3[CH:29]=[C:28]([C:30]([F:32])([F:31])[F:33])[CH:27]=[C:26]([S:43][C:40]4[CH:41]=[CH:42][C:37]([Cl:36])=[CH:38][CH:39]=4)[CH:25]=3)(=[O:23])=[O:22])[CH3:20])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 59192602HCID 59192602, compound

Product 1

HCID 59192540HCID 59192540, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of {(R)-5-[(3-fluoro-5-trifluoromethyl-benzenesulfonyl)-methyl-amino]-5,6,7,8-tetrahydro-naphthalen-1-yloxy}-acetic acid tert-butyl ester (80.0 mg, 0.15 mmol), 4-chloro-benzenethiol (50 μL), and potassium carbonate (55.0 mg, 0.40 mmol) in N,N-dimethylformamide (1.0 mL) was heated in a microwave oven at 150° C. for 30 minutes. The resulting mixture was neutralized with 1N hydrochloric acid and then extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with brine (20 mL×3), dried over anhydrous sodium sulfate, and concentrated in vacuo to afford ((R)-5-{[3-(4-chloro-phenylsulfanyl)-5-trifluoromethyl-benzenesulfonyl]-methyl-amino}-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (67.5 mg, 70.2%) as a viscous oil, which was used for the next step without any further purification. MS cald. for C30H31ClF3NO5S2 641, obsd. 642 (ESI+) [(M+H)+].

Workup

  1. extractionextracted with ethyl acetate (20 mL×3)
  2. washThe combined organic layers were washed with brine (20 mL×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dadd80db3395457783bedaa0331073bc
Source dataset
uspto-grants-2012_04
Patent number
US08163781B2

Reaction notes

Loading…