Water → 2-{(3aR,5R,6R,6aR)-5-[2-(4'-chlorobiphenyl-4-yl)ethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}ethyl methanesulfonate

HRID 84028Notes

Reaction equation

HRID 84028 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C@H:28]3[O:37][C@@H:31]4[O:32][C:33]([CH3:36])([CH3:35])[O:34][C@@H:30]4[C@@H:29]3[CH2:38][CH2:39][OH:40])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.O>ClCCl>[CH3:8][S:9]([O:40][CH2:39][CH2:38][C@H:29]1[C@@H:30]2[C@@H:31]([O:32][C:33]([CH3:36])([CH3:35])[O:34]2)[O:37][C@@H:28]1[CH2:27][CH2:26][C:23]1[CH:22]=[CH:21][C:20]([C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)=[CH:25][CH:24]=1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67182866HCID 67182866, compound

Product 1

HCID 867009772-{(3aR,5R,6R,6aR)-5-[2-(4'-chlorobiphenyl-4-yl)ethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.43 ml) and methanesulfonyl chloride (0.21 mL) were added to a solution of the compound obtained from step i above (0.6 g) in dichloromethane (15 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. Dichloromethane and water were added to reaction mixture. The organic layer was separated, washed with water, dried, and concentrated under reduced pressure to furnish the title compound (0.6 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7f7aa1ad2f943d5ae49812356cd4f74
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Reaction notes

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