{3-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazol-1-yl}-acetic acid tert-butyl ester → {3-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazol-1-yl}-acetic acid

HRID 545991Notes

Reaction equation

HRID 545991 reaction equation
C([O:5][C:6](=[O:34])[CH2:7][N:8]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:33])[C@@H:15]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[C:24]([Cl:32])[CH:23]=2)[CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:9]1)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[Cl:32][C:24]1[CH:23]=[C:22]([C@@H:15]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:14]([NH:13][C:10]2[CH:11]=[CH:12][N:8]([CH2:7][C:6]([OH:34])=[O:5])[N:9]=2)=[O:33])[CH:27]=[CH:26][C:25]=1[S:28]([CH3:31])(=[O:30])=[O:29]

Participants

3

Reactant 1

HCID 67193401{3-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 67189335{3-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazol-1-yl}-acetic acidYield 79%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Conditions

Temperature
25 °C

Procedure

{3-[2(R)-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazol-1-yl}-acetic acid tert-butyl ester (95 mg, 0.19 mmol) was dissolved in 20% trifluoroacetic acid/methylene chloride (2 mL) and allowed to stir at 25° C. for 4 h, after which time the solvent was removed by blowing nitrogen into the reaction vessel. The crude material was purified by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 4 g; 0% ethyl acetate/hexanes to 75% ethyl acetate/hexanes), afforded {3-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazol-1-yl}-acetic acid (67 mg, 79%) as a white powder: ESI-LRMS m/e calcd for C20H24ClN3O5S [M+] 453.1, found 454.1 [M+H+]; 1H NMR (400 MHz, CDCl3) δ ppm 1.03-1.24 (m, 2H, CH2), 1.37-1.97 (m, 8H, 4×CH2), 2.12-2.26 (m, 1H, CH), 3.26 (s, 3H, SO2CH3), 3.62 (t, J=7.5 Hz, 1H, CH), 4.72 (AB, Jgem=17.4 Hz, 2H, NCH2), 6.82 (d, J=1.2, 1H, Ar), 7.39 (d, J=1.2, 1H, Ar), 7.43 (d, Jo=8.2 Hz, 1H, Ar), 7.58 (s, 1H, Ar), 8.01 (d, Jo=8.2 Hz, 1H, Ar), 9.82 (s, 1H, NH).

Workup

  1. customafter which time the solvent was removed
  2. customThe crude material was purified by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 4 g; 0% ethyl acetate/hexanes to 75% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8a92fb9a54324100bd875a23fa38bd01
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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