Dichloromethane → HCID 69669853, compound

HRID 469916Notes

Reaction equation

HRID 469916 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]1([C:29]([OH:31])=[O:30])[C@H:14]([CH2:15][S:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([CH3:24])[CH:18]=2)[C@@H:13]([OH:25])[C@@H:12]2[C@H:10]1[C@H:11]2[C:26]([OH:28])=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].S(Cl)(O[CH2:41][Cl:42])(=O)=O.[Cl:44][CH2:45]Cl>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:44][CH2:45][O:30][C:29]([C@:9]1([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@H:14]([CH2:15][S:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([CH3:24])[CH:18]=2)[C@@H:13]([OH:25])[C@@H:12]2[C@H:10]1[C@H:11]2[C:26]([O:28][CH2:41][Cl:42])=[O:27])=[O:31]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 2733556Chloromethyl chlorosulfateHCID 69669873HCID 69669873, compound

Product 1

HCID 69669853HCID 69669853, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×

Procedure

To a stirring mixture of (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (2.4 g, 5.27 mmol), tetra(n-butyl)ammonium bisulfate (178.90 mg, 526.89 μmoles), and sodium bicarbonate (3.54 g, 42.15 mmol) in dichloromethane (13.2 mL) and water (13.2 mL) is added chloromethyl chlorosulfate (1.20 mL, 11.59 mmol). The mixture is stirred at ambient temperature for 18 hours. The reaction is poured over water and extracted with dichloromethane. The combined organics are dried over magnesium sulfate, filtered and concentrated to give a residue. The residue is purified by flash chromatography (20-35% ethyl acetate/hexane) to give the title compound (1.37 g, 2.48 mmol, 47% yield). MS (m/z): 574.0 (M+Na).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organics are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue
  6. customThe residue is purified by flash chromatography (20-35% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2ded6a2cd3b44aac820f845d895eddd1
Source dataset
uspto-grants-2014_01
Patent number
US08629169B2

Reaction notes

Loading…