Dimethylformamide → HCID 118667047, compound

HRID 591531Notes

Reaction equation

HRID 591531 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:17]=[CH:16][C:9]2[C@H:10]([CH2:13][CH2:14][SH:15])[CH2:11][O:12][C:8]=2[CH:7]=1.CCN(C(C)C)C(C)C.CN(C=O)C.Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>O>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][S:15][CH2:14][CH2:13][C@H:10]1[C:9]2[CH:16]=[CH:17][C:6]([O:5][CH2:4][C:3]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:2]=3[Cl:1])=[CH:7][C:8]=2[O:12][CH2:11]1)[CH3:43]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 89767825HCID 89767825, compound

Product 1

HCID 118667047HCID 118667047, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanethiol (30 mg), DIPEA (0.029 mL) and DMF (dry) (15 mL) was added ethyl 2-bromoacetate (21.15 mg). The mixture was stirred at room temperature under argon atmosphere overnight. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (25.0 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-c4b7f346e08849e1a07f203c0c28d8c7
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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