Water → HCID 66976868, compound

HRID 1022786Notes

Reaction equation

HRID 1022786 reaction equation
Cl[CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].[NH2:8][CH2:9][C@H:10]1[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][C@H:11]1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=1.C(N(CC)CC)C.O>C1COCC1>[Cl:31][C:26]1[CH:25]=[C:24]([C@H:11]2[C@@H:10]([CH2:9][NH:8][S:4]([CH:3]=[CH2:2])(=[O:6])=[O:5])[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]2)[CH:29]=[CH:28][C:27]=1[Cl:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 66975545HCID 66975545, compound

Product 1

HCID 66976868HCID 66976868, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloroethanesulfonyl chloride (390 mg) was added dropwise to a solution of tert-butyl (6R,7S)-7-(aminomethyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (600 mg) and triethylamine (0.67 mL) in THF (5 mL), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (235 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ad8593f83ea54ff793ef6460b539ac72
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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