Trifluoroacetic acid → HCID 59192618, compound

HRID 1696876Notes

Reaction equation

HRID 1696876 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C@@H:14]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:13]=2[CH:12]=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:35][C:32]1[CH:33]=[CH:34][C:29]([C:26]2[CH:25]=[CH:24][C:23]([S:20]([NH:19][C@@H:14]3[CH2:15][CH2:16][CH2:17][C:18]4[C:9]([O:8][CH2:7][C:6]([OH:36])=[O:5])=[CH:10][CH:11]=[CH:12][C:13]3=4)(=[O:22])=[O:21])=[CH:28][CH:27]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59192608HCID 59192608, compound

Product 1

HCID 59192618HCID 59192618, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude [(R)-5-(4′-methyl-biphenyl-4-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester was treated with 10% trifluoroacetic acid (0.02 mL) in dichloromethane (1 mL) at room temperature for 2 hours. The mixture was concentrated in vacuo. The residue was purified by reverse phase HPLC (Pursuit C-18, 20×150 mm, water/acetonitrile/0.05% trifluoroacetic acid) to give [(R)-5-(4′-methyl-biphenyl-4-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid (4.3 mg, 9.5% over two steps). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.02 (br. s, 1H), 8.13 (d, J=8.5 Hz, 1H), 7.78-8.00 (m, 4H), 7.68 (d, J=8.0 Hz, 2H), 7.33 (d, J=8.0 Hz, 2H), 7.03 (t, J=7.9 Hz, 1H), 6.73 (d, J=7.9 Hz, 1H), 6.66 (d, J=7.9 Hz, 1H), 4.62 (s, 2H), 4.29-4.44 (m, 1H), 2.42-2.62 (m, 2H), 2.37 (s, 3H), 1.79 (br. s, 1H), 1.56 (d, 3H); MS cald. for C25H25NO5S 451, obsd. 452 [(M+H)+].

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by reverse phase HPLC (Pursuit C-18, 20×150 mm, water/acetonitrile/0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-fbdfdf65e04a4abaaf8fa801a0b39d69
Source dataset
uspto-grants-2012_04
Patent number
US08163781B2

Reaction notes

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