Water → HCID 68440870, compound

HRID 2246953Notes

Reaction equation

HRID 2246953 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C@@H:11]([CH2:42][C:43]([CH3:46])([OH:45])[CH3:44])[CH2:10]2)=[CH:5][CH:4]=1.[H-].[K+].[CH3:49][N:50]([CH3:54])[C:51](Cl)=[O:52].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C@@H:11]([CH2:42][C:43]([O:45][C:51](=[O:52])[N:50]([CH3:54])[CH3:49])([CH3:46])[CH3:44])[CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 82127Potassium hydrideHCID 68441598HCID 68441598, compound

Product 1

HCID 68440870HCID 68440870, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 120 mg of 1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-2-methyl-propan-2-ol (from example 57b) in 0.5 ml of tetrahydrofuran are added 80 mg potassium hydride (35% dispersion in oil). The reaction mixture is stirred for 1 hour and then 163 μl dimethylcarbamoyl chloride are added. The mixture is stirred at room temperature for 18 hours. The mixture is treated with 2 ml water and extracted with 50 ml ethyl acetate (2×). The combined organic layers are washed with brine and dried with sodium sulfate. The organic layer is filtered and evaporated under reduced pressure. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a yellow solid. Rf=0.45 (EtOAc-heptane 2:1); Rt=5.59.

Workup

  1. stirringThe mixture is stirred at room temperature for 18 hours
  2. extractionextracted with 50 ml ethyl acetate (2×)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationThe organic layer is filtered
  6. customevaporated under reduced pressure
  7. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-9b67c57e946646478c4f937330fc1653
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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