Sodium Thiosulfate → HCID 58674963, compound

HRID 1809483Notes

Reaction equation

HRID 1809483 reaction equation
[C:1]([O:5][C:6](=[O:40])[CH2:7][CH:8]([NH:13][C:14](=[O:39])[C@@H:15]([N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:24]1=[O:38])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]([OH:12])[CH2:10][F:11])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:40])[CH2:7][CH:8]([NH:13][C:14](=[O:39])[C@@H:15]([N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:24]1=[O:38])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9](=[O:12])[CH2:10][F:11])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58674952HCID 58674952, compound

Product 1

HCID 58674963HCID 58674963, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 3(R,S)-[2(S)-(3-benzoylamino-2-oxo-2H-pyridin-1-yl)-3-phenyl-propionylamino]-5-fluoro-4(R,S)-hydroxy-pentanoic acid tert-butyl ester (1.23 g, 2.23 mmol) in anhydrous DCM (25 mL) was treated with 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane) (1.13 g, 2.67 mmol) at 0° C. The resulting mixture was kept at 0° C. for 2 hours, diluted with ethyl acetate, then poured into a 1:1 mixture of saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium thiosulfate. The organic layer was removed and the aqueous layer re-extracted with ethyl acetate. The combined organic extracts were dried (Magnesium sulfate) and concentrated. The residue was purified by flash chromatography (40-60% ethyl acetate/petrol ether) to afford the title compound as a red gum (776 mg, 64%); 1H NMR (400 MHz, CDCl3) δ 1.32-1.40 (3H, s), 2.60 (1H, m), 2.92 (1H, m), 3.27 (1H, m), 3.61 (1H, m), 4.78-4.88 (1H, m), 4.97-5.05 (2H, m), 5.77 (1H, m), 6.43 (1H, m), 7.22-7.38 (7H, m), 7.54-7.65 (3H, m), 7.95 (2H, m), 8.62 (1H, m), 9.22 (1H, m).

Workup

  1. customThe organic layer was removed
  2. extractionthe aqueous layer re-extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (Magnesium sulfate)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (40-60% ethyl acetate/petrol ether)

Sources & evidence

ORD record
ord-6bc6606e53214f0891ae58a13596291e
Source dataset
uspto-grants-2013_01
Patent number
US08362043B2

Reaction notes

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