Sodium Thiosulfate → HCID 18752818, compound

HRID 1838102Notes

Reaction equation

HRID 1838102 reaction equation
[CH3:1][CH:2]([NH:4][C:5](=[O:28])[C:6]([F:27])([F:26])[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])=[O:17])[OH:8])[CH3:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(O)(C)(C)C.C(Cl)Cl>[CH3:3][CH:2]([NH:4][C:5](=[O:28])[C:6]([F:27])([F:26])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])=[O:17])=[O:8])[CH3:1]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 18752827HCID 18752827, compound

Product 1

HCID 18752818HCID 18752818, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of N-[2-(3-(2-propylamino)-3-oxo-2,2-difluoro-1-hydroxypropyl)phenyl]-2-methoxyphenylcarboxamide of Step 4 (200 mg, 0.51 mmol), CH2Cl2 (5 mL) and tert-butanol (5 mL), was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxyl-3(1H)-one (1.5 g, 3.54 mmol) under argon at 23° C. After 18 h, sat. NaHCO3 (10 mL) was added followed by solid Na2S2O3 (1.0 g, 6.3 mmol). After 2 h of vigorous stirring at 23° C., the organic layer was separated, washed with sat. NaHCO3 (2×10 mL), sat. Na2S2O3 (2×10 mL), and brine (1×10 mL) and dried (MgSO4). Upon concentration in vacuo and trituration with ethyl ether, the title compound was afforded (100 mg) as a yellow solid : mp 131.5-132° C. 1H NMR (CDCl3) δ1.27 (d), 4.13 (s,), 4.13-4.20 (m), 6.32 (br d), 7.04 (m), 7.10 (m), 7.19 (m), 7.51 (m) 7.67 (m), 8.11 (m), 8.22 (m), 8.90 (m), 12.01 (br s). MS (EI) 390 (M+), 254, 135. Anal. Calc'd. for C20H20F2N2O4 plus 0.25 mol H2O: C, 60.83; H, 5.23; N, 7.09. Found: C, 60.75; H, 5.00; N, 6.95.

Workup

  1. customthe organic layer was separated
  2. washwashed with sat. NaHCO3 (2×10 mL), sat. Na2S2O3 (2×10 mL), and brine (1×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationUpon concentration in vacuo and trituration with ethyl ether

Sources & evidence

ORD record
ord-458ce334b2fa40819f0d06623204ac30
Source dataset
uspto-grants-2004_01
Patent number
US06673788B2

Reaction notes

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