2-Methoxypropene → HCID 59511564, compound

HRID 1158508Notes

Reaction equation

HRID 1158508 reaction equation
[CH2:1]([C@:8]([OH:42])([CH2:22][CH2:23][O:24][Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:9]([NH:11][C@H:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][C@H:13]1[OH:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:43]1(C)[CH:48]=CC(S(O)(=O)=O)=C[CH:44]=1.[NH+]1C=CC=CC=1.COC(C)=C.C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([C@:8]([OH:42])([CH2:22][CH2:23][O:24][Si:25]([C:38]([CH3:39])([CH3:41])[CH3:40])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:9]([N:11]1[C@H:12]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:14][C@H:13]2[O:21][C:43]1([CH3:48])[CH3:44])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 83002-MethoxypropeneHCID 516892Sodium BicarbonateHCID 22033616Pyridinium.p-toluenesulfonateHCID 44818262HCID 44818262, compound

Product 1

HCID 59511564HCID 59511564, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of (S)-2-benzyl-4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-N-((1S,2R)-2-hydroxy-indan-1-yl)-butyramide (21e) (0.325 g, 0.56 mmol) and pyridinium p-toluenesulphonic acid (15 mg, 0.05 mmol) in dry dichloromethane (20 mL), 2-methoxypropene (0.4 g, 5.6 mmol) was added and stirred for 6 h at the same temperature. Saturated NaHCO3 solution was added, organic layer and washed with sat. NaHCO3, brine, dried over anhydrous MgSO4 and evaporated under reduced pressure. The crude title product [(0.33 g), MS (ESI+): 620 (M+)] was used as such for the next reaction.

Workup

  1. additionwas added
  2. washorganic layer and washed with sat. NaHCO3, brine
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated under reduced pressure
  5. customsuch for the next reaction

Sources & evidence

ORD record
ord-dfae9ea596554fbf914102b8a1f25b49
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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