Sodium Thiosulfate → HCID 86585878, compound

HRID 988015Notes

Reaction equation

HRID 988015 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][CH:8]([NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:9]([OH:12])[CH2:10][F:11])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.CCOC(C)=O>[C:1]([O:5][C:6](=[O:22])[CH2:7][CH:8]([NH:13][C:14](=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9](=[O:12])[CH2:10][F:11])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 69837235HCID 69837235, compound

Product 1

HCID 86585878HCID 86585878, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,1,1-Triacetoxy-1,1-dihydro-1,2-benzodioxol-3(1H)-one (273 mg, 0.64 mmol) was added in one portion to a stirred solution of 3-benzoylamino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester (100 mg, 0.32 mmol) (prepared from benzoic acid and 3-amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester using standard coupling procedures eg. HOBT, DMAP, and EDC) in dry dichloromethane (DCM) (2 ml) at 0° C. The mixture was brought to room temperature (r.t.) during 16 h, diluted with EtOAc, then poured into a 1:1 mixture of saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium thiosulphate. The organic layer was removed and the aqueous layer re-extracted with EtOAc. The combined organic organic extracts were dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (30% EtOAc in hexane) to afford the title compound as a colourless gum (94 mg, 95%): 1H NMR (CDCl3) δ 7.80 (2H, m), 7.50 (4H, m), 5.2 (3H, m), 2.95 (2H, m), 1.45 (9H, s); 13C NMR (CDCl3) δ 203.19, 203.02, 171.02, 167.57, 133.54, 133.04, 132.60, 129.16, 127.97, 127.53, 85.52, 83.70, 82.80, 53.13, 53.03, 36.63, 36.61, 28.44, 28.37; 19F NMR (CDCl3) δ −232.09(t, J 49 Hz).

Workup

  1. customwas brought to room temperature
  2. custom(r.t.)
  3. customduring 16 h
  4. customThe organic layer was removed
  5. extractionthe aqueous layer re-extracted with EtOAc
  6. dry with materialThe combined organic organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-011b69b576ca4b78a49bcfca4b7d5295
Source dataset
uspto-grants-2003_10
Patent number
US06632962B2

Reaction notes

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