Potassium Carbonate → HCID 67032056, compound

HRID 599476Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:35])[C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([S:19][C:20]3[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:23]([OH:30])=[C:22]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:21]=3)[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:8][CH:9]=1)=[O:4].Br[CH2:37][CH2:38][CH2:39][OH:40].C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:35])[C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([S:19][C:20]3[CH:25]=[C:24]([C:26]([CH3:27])([CH3:28])[CH3:29])[C:23]([O:30][CH2:37][CH2:38][CH2:39][OH:40])=[C:22]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:21]=3)[CH2:15][CH2:14]2)(=[O:11])=[O:12])=[CH:8][CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 75 °C

Procedure

To 5-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (Ex. 4a, 436 mg, 0.83 mmol) in 3 mL of DMF was added 3-bromo-propan-1-ol (127 mg, 0.91 mmol) and K2CO3 (343 mg, 2.5 mmol). The mixture was heated to 75° C. for 16 h. Upon cooling to room temperature it was poured into saturated NH4Cl (30 mL). The mixture was extracted with Ethyl acetate (3×30 mL) and the organic extracts were dried over Na2SO4 and concentrated under reduced pressure. Chromatography (3-40% Ethyl acetate/hexanes) gave 5-{4-[3,5-di-tert-butyl-4-(3-hydroxy-propoxy)-phenylsulfanyl]-piperidine-1-sulfonyl}-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester as a pale-yellow thick oil (203 mg). ESI/CI-MS m/z 581 ([M+H]+).

Workup

temperatureUpon cooling to room temperature it
extractionThe mixture was extracted with Ethyl acetate (3×30 mL)
dry with materialthe organic extracts were dried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-faec37cb3c7745f390aeae08f82b2ee8
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897776B2

Reaction notes

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