Potassium Carbonate → HCID 67431557, compound

HRID 454978Notes

Reaction equation

HRID 454978 reaction equation
[OH:1][CH2:2][C@H:3]([NH:11][C:12]([C@H:14]1[CH2:16][C@@H:15]1[C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH2:22]([CH:24]([CH2:27][CH3:28])[CH2:25]Br)[CH3:23].C([O-])([O-])=[O:30].[K+].[K+]>CN(C=O)C.CCOCC>[OH:1][CH:2]([OH:30])[C@H:3]([NH:11][C:12]([C@H:14]1[CH2:16][C@@H:15]1[C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:25][CH:24]([CH2:27][CH3:28])[CH2:22][CH3:23])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 77432Pentane, 3-(bromomethyl)-HCID 67432092HCID 67432092, compound

Product 1

HCID 67431557HCID 67431557, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (1S,2S)-2-thiophen-2-yl-cyclopropanecarboxylic acid [(R)-2-hydroxy-1-[4-hydroxy-phenyl)-ethyl]-amide (35 mg, 0.105 mmol) dissolved in 0.8 mL DMF was added the 2-ethylbutyl bromide (38 mg, 0.231 mmol) followed by K2CO3 (32 mg, 0.231 mmol). It was heated to 60° C. with stirring overnight. On the next day it was cooled to rt, diluted with ether and quenched with water. The organic layer was washed with water and brine, dried over MgSO4, and concentrated. It was then purified by flash column (20-40% EtOAc in DCM) to afford the titled compound (26 mg, 58%). 1H NMR (400 MHz, MeOD) δ ppm 5.8 (d, J=8.6 Hz, 2 H), 5.7 (dd, J=5.2, 1.1 Hz, 1H), 5.4 (d, J=8.6 Hz, 3H), 5.3 (d, J=3.5 Hz, 1H), 3.4-3.5 (m, 1H), 2.4 (d, J=5.6 Hz, 2H), 2.2 (dd, J=6.6, 3.0 Hz, 2H), 1.0 (dd, J=6.3, 2.5 Hz, 1H), 0.5 (ddd, J=8.6, 4.7, 4.4 Hz, 1H), 0.1-0.2 (m, 1H), −0.1-0.1 (m, J=15.1, 7.7, 7.6, 7.6 Hz, 5H), −0.2 (ddd, J=8.5, 6.2, 4.3 Hz, 1H), −0.5 (t, J=7.5 Hz, 6H). LRMS (ESI)=388, [(M+1)+ calcd for C22H30NO3S 387.5].

Workup

  1. temperatureOn the next day it was cooled to rt
  2. customquenched with water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customIt was then purified by flash column (20-40% EtOAc in DCM)

Sources & evidence

ORD record
ord-11aab01228814762af58d7d08c8b3d79
Source dataset
uspto-grants-2013_07
Patent number
US08497271B2

Reaction notes

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