Water → HCID 69018943, compound

HRID 1865080Notes

Reaction equation

C(N(S(F)(F)[F:7])CC)C.[CH2:10]([O:12][C:13]([C:15]1[N:16]([CH3:41])[C:17]([CH2:39][CH3:40])=[C:18]([C:37]#[N:38])[C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH:26](O)[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]#[N:35])[CH:29]=2)=[CH:22][CH:21]=1)=[O:14])[CH3:11].O>C(Cl)Cl>[CH2:10]([O:12][C:13]([C:15]1[N:16]([CH3:41])[C:17]([CH2:39][CH3:40])=[C:18]([C:37]#[N:38])[C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([F:7])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]#[N:35])[CH:29]=2)=[CH:22][CH:21]=1)=[O:14])[CH3:11]

Participants

Conditions

Temperature: -78 °C

Procedure

Add (diethylamino)sulfur trifluoride (145 uL, 1.1 mmol) to 4-cyano-3-{4-[2-(3-cyano-phenyl)-1-hydroxy-ethyl]-phenyl}-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.427 g, 1.0 mmol, prepared in example E-163) in methylene chloride with stirring at −78° C. After 30 minutes, gradually allow the reaction mixture to warm to ambient temperature. After 2 hours, pour the reaction mixture into water and extract with methylene chloride. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with ethyl acetate:hexanes to provide the title compound. Mass spectrum (m/e): 430.0 (M+1).

Workup

temperatureto warm to ambient temperature
waitAfter 2 hours
extractionextract with methylene chloride
washwash with water and brine
dry with materialdry over anhydrous magnesium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customPurify the residue by flash chromatography
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-4763138781fc415eaf1dd5f861b45682
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

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