Sodium Bicarbonate → HCID 86668886, compound

HRID 1524646Notes

Reaction equation

HRID 1524646 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@:8]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C@H:12]([CH2:13][OH:14])[C@@H:11]([CH3:15])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CCCCCC.CCOC(C)=O.C([O-])(O)=O.[Na+].S(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[NH:7][C@:8]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C@H:12]([CH:13]=[O:14])[C@@H:11]([CH3:15])[O:10][CH2:9]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 21226206Ethyl acetate hexaneHCID 23665763Sodium BisulfiteHCID 66870094HCID 66870094, compound

Product 1

HCID 86668886HCID 86668886, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(3S,4R,5R)-3-(2-Fluoro-phenyl)-4-hydroxymethyl-5-methyl-tetrahydro-furan-3-yl]-carbamic acid tert-butylester (Preparation Example 30-(1)) (1.2 g, 3.60 mmol) dissolved in DCM (26.5 g, 20 mL). 1,1,1-tris(acetyloxy)-,2-benziodoxol-3(1H)-one (3.12 g, 7.3 mmol) was added. The reaction mixture was stirred at RT. The reaction was followed by TLC Hexane/EtOAc 40%. Product Rf was 0.52. The reaction reached completion after 2 h. Work up: 20 ml of sat. aq. NaHCO3 and 20 ml of saturated sodium bisulfite was added. The mixture was then extracted with ether 3×50 ml. The combined organic phases were dried on MgSO4, concentrated and purified by flash chromatography Hexane/EtOAc (5-30%). 900 mg of the title compound was isolated (76% yield).

Workup

  1. customafter 2 h
  2. extractionThe mixture was then extracted with ether 3×50 ml
  3. customThe combined organic phases were dried on MgSO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography Hexane/EtOAc (5-30%)

Sources & evidence

ORD record
ord-f43aec0eec074f00a19bb7b8816ec849
Source dataset
uspto-grants-2015_07
Patent number
US09079914B2

Reaction notes

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