Triethylamine → tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylate

HRID 1022603Notes

Reaction equation

HRID 1022603 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([C@@H:14]2[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][C@H:15]2[CH2:28][OH:29])[CH:10]=[CH:11][C:12]=1[Cl:13].C(N(CC)CC)C>C1COCC1.C(=O)([O-])O.[Na+]>[Cl:6][C:7]1[CH:8]=[C:9]([C@@H:14]2[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:16][C@H:15]2[CH2:28][O:29][S:2]([CH3:1])(=[O:4])=[O:3])[CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66975404tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-(hydroxymethyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 86663851tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylateYield 96.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Methanesulfonyl chloride (1.366 mL, 17.65 mmol) was added dropwise to a solution of tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (5.11 g, 13.58 mmol) and triethylamine (2.84 mL, 20.37 mmol) in THF (50 mL) under ice-cooling, and the mixture was stirred under ice-cooling for 2 hr. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated to give the title compound (5.95 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-40bb5536108143c683cb3576c571ce59
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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