Sodium Acetate → HCID 57461521, compound

HRID 1663206Notes

Reaction equation

HRID 1663206 reaction equation
[CH:1]1([CH2:7][CH:8]([N:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:30])[CH:26]=3)[N:21]=[CH:20]2)[C:9]([NH:11][C:12]2[S:13][C:14]([CH:17]=[O:18])=[CH:15][N:16]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC([O-])=O.[Na+].[BH3-]C#N.[Na+]>C(Cl)Cl.CO>[CH:1]1([CH2:7][CH:8]([N:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:30])[CH:26]=3)[N:21]=[CH:20]2)[C:9]([NH:11][C:12]2[S:13][C:14]([CH2:17][OH:18])=[CH:15][N:16]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 57461517HCID 57461517, compound

Product 1

HCID 57461521HCID 57461521, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of Compound 150 (0.2 g, 0.4675 mmol) and NaOAc (46 mg, 0.561 mmol) was dissolved in DCM:MeOH (20:1, 1 mL) and stirred for 30 min. To this solution was added NaBH3CN (0.056 mg, 0.891 mmol) and the mixture was stirred at RT overnight. The reaction was quenched with aqueous NaHCO3 and extracted into DCM. The organic layer was washed with water and dried over MgSO4. The crude product was purified via preparative HPLC. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.88-1.31 (m, 6H) 1.73 (s, 5H) 1.99-2.10 (m, 1 H) 2.14-2.26 (m, 1H) 4.82 (s, 2H) 5.83 (dd, J=8.84, 7.07 Hz, 1H) 7.47 (s, 1H) 7.48-7.56 (m, 1H) 7.77 (dd, J=8.97, 4.67 Hz, 1H) 7.95 (dd, J=8.34, 2.78 Hz, 1H) 8.31 (s, 1H). [M+H] calc'd for C21H23FN4O3S, 431; found, 431.

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. customThe reaction was quenched with aqueous NaHCO3
  3. extractionextracted into DCM
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. customThe crude product was purified via preparative HPLC

Sources & evidence

ORD record
ord-cb99a3d5c4bf41b79161978412b5e487
Source dataset
uspto-grants-2011_10
Patent number
US08034822B2

Reaction notes

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