Dimethyl Sulfoxide → HCID 15871736, compound

HRID 1738905Notes

Reaction equation

HRID 1738905 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][OH:25])[C:20](=[O:28])[C@@H:19]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:18][C@H:17]([C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][CH:36]=3)[C:16]=2[CH:45]=1.C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH2:22][C:23]([CH:24]=[O:25])([CH3:26])[CH3:27])[C:20](=[O:28])[C@@H:19]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:18][C@H:17]([C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][CH:36]=3)[C:16]=2[CH:45]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15871735HCID 15871735, compound

Product 1

HCID 15871736HCID 15871736, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Dimethyl sulphoxide (1.61 g, 20.6 mmol) was added dropwise to a solution of oxalyl chloride (1.31 g, 10.3 mmol) in dichloromethane (75 ml) at -60° C. The mixture was stirred until gas evolution had ceased. Ethyl trans-7-chloro-5-(1-naphthyl)-1-(2,2-dimethyl-3-hydroxypropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate (4.6 g, 9.4 mmol), dissolved in dichloromethane (30 ml), was added dropwise over a period of 5 min. at -60° C., and stirring was continued for further 15 min. The mixture was quenched with triethylamine (4.73 g, 46.8 mmol) before allowing to warm to room temperature. Addition of water, separation of the organic layer and repeated extraction of the aqueous layer with dichloromethane was followed by drying of the combined organic layers with MgSO4. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography (dichloromethane/methanol 99:1) to give the title compound (4.62 g, 99%).

Workup

  1. additionwas added dropwise over a period of 5 min. at -60° C.
  2. stirringstirring
  3. extractionextraction of the aqueous layer with dichloromethane
  4. dry with materialby drying of the combined organic layers with MgSO4
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by flash chromatography (dichloromethane/methanol 99:1)

Sources & evidence

ORD record
ord-da57ee2899e9491aa81ab5aa6eb9bc70
Source dataset
uspto-grants-1999_10
Patent number
US05965553

Reaction notes

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