Ethanol → HCID 67191160, compound

HRID 546222Notes

Reaction equation

HRID 546222 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:35])[C@@H:16]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[C:26]([CH3:34])[CH:25]=2)[CH2:17][C@H:18]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]2)=[N:10]1)(C)(C)C.C(O)C>Cl.C(#N)C>[OH:6][CH2:7][CH2:8][N:9]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:35])[C@@H:16]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[C:26]([CH3:34])[CH:25]=2)[CH2:17][C@H:18]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19]2)=[N:10]1

Participants

5

Reactant 2

HCID 702EthanolHCID 67189552HCID 67189552, compound

Product 1

HCID 67191160HCID 67191160, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

In a flask containing (R)—N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-yl}-2-(4-methanesulfonyl-3-methyl-phenyl)-3-((R)-3-oxo-cyclopentyl)-propionamide (100 mg, 0.18 mmol) was added ethanol (3 mL) and concentrated hydrochloric acid (three drops) and it was stirred at 25° C. for 45 min. It was then diluted with acetonitrile and absorbed onto silica gel (2 g) in vacuo and purified on Biotage Flash chromatography system (40S column, silica gel, 80% ethyl acetate/hexanes to 10% methanol/ethyl acetate) to afford (R)—N-[1-(2-hydroxy-ethyl)-1H-pyrazol-3-yl]-2-(4-methanesulfonyl-3-methyl-phenyl)-3-((R)-3-oxo-cyclopentyl)-propionamide (55 mg, 69%) as a yellow foam: [α]32589=−73.6° (c=0.14, methanol); ES-HRMS m/e calcd for C21H27N3O5S (M+H)+ 434.1745, observed 434.1745; 1H NMR (400 MHz, DMSO-d6) δ 1.51 (m, 1H, CH), 1.77-2.28 (m, 8H, 4×CH2), 2.63 (s, 3H, ArCH3), 3.18 (s, 3H, SO2CH3), 3.67 (q, J=5.5 Hz, 2H, OCH2), 3.91 (m, 1H, ArCHCO), 3.99 (t, J=5.5 Hz, 2 H, NCH2), 4.82 (t, J=5.5 Hz, 1H, OH), 6.41 (d, J=2.2 Hz, 1H, Ar), 7.46 (brs, 1H, Ar), 7.47 (brd, 1H, Ar), 7.53 (d, J=2.2 Hz, 1H, Ar), 7.86 (d, Jo=8.5 Hz, 1H, Ar), 10.77 (s, 1H, NH).

Workup

  1. customabsorbed onto silica gel (2 g) in vacuo
  2. custompurified on Biotage Flash chromatography system (40S column, silica gel, 80% ethyl acetate/hexanes to 10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-b5a89a04da39412fba97485e316bfe5f
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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