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Sodium Bicarbonate → HCID 57671322, compound

HRID 1013828
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Reaction equation

HRID 1013828 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=2)[CH:5]=[C:6]([Cl:36])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][C@@H:12]([CH2:14][O:15]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:11][C:10]1=[O:35].C(=O)(O)[O-].[Na+]>ClCCl.CO.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:37]2[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=2)[CH:5]=[C:6]([Cl:36])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][C@@H:12]([CH2:14][OH:15])[O:11][C:10]1=[O:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 67316423(3R,5S)-3-(3,5-Dichloro-4'-fluoro-biphenyl-4-ylmethyl)-5-trityloxymethyl-dihydro-furan-2-one

Product 1

HCID 57671322HCID 57671322, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent
HCID 6344DichloromethaneSolvent

Procedure

Redissolve (3R,5S)-3-(3,5-Dichloro-4′-fluoro-biphenyl-4-ylmethyl)-5-trityloxymethyl-dihydro-furan-2-one in 30 mL of dichloromethane and 50 mL of methanol containing 0.5 mL of concentrate HCl. Stir the mixture overnight and neutralize with aqueous sodium bicarbonate. Most of the methanol and dichloromethane are removed. Extract the product with ethyl acetate. Wash the organic layers with water and then brine. Evaporate the solvent and chromatograph the product on flash silica gel using 5 to 25% acetone in methylene chloride. Evaporate the product containing fractions and recrystallize from ethyl acetate and heptane to afford 2.5 g (44% yield) of (3R,5S)-3-(3,5-dichloro-4′-fluoro-biphenyl-4-ylmethyl)-5-hydroxymethyl-dihydro-furan-2-one.

Workup

  1. customMost of the methanol and dichloromethane are removed
  2. extractionExtract the product with ethyl acetate
  3. washWash the organic layers with water
  4. customEvaporate the solvent and chromatograph the product on flash silica gel using 5 to 25% acetone in methylene chloride
  5. customEvaporate the product
  6. additioncontaining fractions
  7. customrecrystallize from ethyl acetate and heptane

Sources & evidence

ORD record
ord-7cb0dff77a8c45248f9ca16e3cc4e13b
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981918B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes