Dimethylformamide → HCID 69597614, compound

HRID 1796801Notes

Reaction equation

HRID 1796801 reaction equation
[CH3:1][C:2]1([CH3:11])[C@H:7]2[NH:8][CH2:9][C@H:4]([O:5][C:6]2=[O:10])[CH2:3]1.CN(C)C=O.C(N(CC)CC)C.[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>Cl>[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([N:8]2[CH2:9][C@H:4]3[CH2:3][C:2]([CH3:11])([CH3:1])[C@@H:7]2[C:6](=[O:10])[O:5]3)(=[O:40])=[O:39])=[CH:34][CH:33]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 47383854-(Benzyloxy)benzene-1-sulfonyl chlorideHCID 45082134HCID 45082134, compound2×

Product 1

HCID 69597614HCID 69597614, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (1R,4R)-8,8-dimethyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (compound of formula XXXVI, 10 mmol) and dimethylformamide (20 ml) at about 0° C. was treated with triethylamine (10–20 mmol) and 4-benzyloxybenzenesulfonyl chloride (15 mmol). After stirring for about 1 hours, the mixture is warmed to a temperature of about 20° C. to about 25° C. and stirred for about an additional 12 hours. The mixture is diluted with 1M hydrochloric acid, extracted twice with ethyl acetate, and the combined organic layers are dried over sodium sulfate, filtered and concentrated in vacuo to give (1R,4R)-5-(4-benzyloxy-benzenesulfonyl)-8,8-dimethyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one as a colorless syrup.

Workup

  1. temperaturethe mixture is warmed to a temperature of about 20° C. to about 25° C.
  2. stirringstirred for about an additional 12 hours
  3. extractionextracted twice with ethyl acetate
  4. dry with materialthe combined organic layers are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d91774e5319b427eabc8856bf1c338dc
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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