Triethylamine → 1-[4-(3-t-Butyldiphenylsilyloxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]-3-methanesulfonyloxyazetidine

HRID 891817Notes

Reaction equation

HRID 891817 reaction equation
[Si:1]([O:18][CH:19]1[CH2:22][N:21]([C:23]([C:25]2[N:26]=[C:27]([N:30]3[CH2:33][CH:32]([OH:34])[CH2:31]3)[O:28][CH:29]=2)=[O:24])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37].C(N(CC)CC)C>C(Cl)Cl>[Si:1]([O:18][CH:19]1[CH2:20][N:21]([C:23]([C:25]2[N:26]=[C:27]([N:30]3[CH2:33][CH:32]([O:34][S:36]([CH3:35])(=[O:38])=[O:37])[CH2:31]3)[O:28][CH:29]=2)=[O:24])[CH2:22]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 222429771-[4-(3-t-Butyldiphenylsilyloxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]-3-hydroxyazetidine

Product 1

HCID 222428271-[4-(3-t-Butyldiphenylsilyloxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]-3-methanesulfonyloxyazetidineYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[4-(3-t-butyldiphenylsilyloxyazetidine-l-carbonyl)-1,3-oxazol-2-yl]-3-hydroxyazetidine (1.68 g, 3.53 mmol) (obtained as described in Reference Example 74(1)) in methylene chloride (84 ml) were added methanesulfonyl chloride (820 μl, 10.6 mmol) and triethylamine (1.49 ml, 10.6 mmol) in an ice bath and the mixture was stirred for 10 minutes and then at room temperature for 0.5 hour. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using methylene chloride:ethyl acetate (1:1) as the eluant to afford 1-[4-(3-t-butyldiphenylsilyloxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]-3-methanesulfonyloxyazetidine (1.56 g, yield 80%) as a pale yellow solid.

Workup

  1. waitat room temperature for 0.5 hour
  2. customthe completion of the reaction
  3. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-309ea92eb784489fb94c153b086e87a5
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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