Acetic Acid → HCID 68985012, compound

HRID 1467895Notes

Reaction equation

HRID 1467895 reaction equation
[NH2:1][CH:2]([CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH:26]2[CH2:28][CH2:27]2)[S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1)=[O:5].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:37](C)=O.[Na+].CC(O)=O>CO.CCOC(C)=O>[CH:26]1([N:12]([CH:9]2[CH2:10][CH2:11][N:6]([C:4](=[O:5])[CH2:3][CH:2]([NH:1][CH3:37])[CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:7][CH2:8]2)[S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)(=[O:15])=[O:14])[CH2:27][CH2:28]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68984655HCID 68984655, compound

Product 1

HCID 68985012HCID 68985012, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of a compound 46 prepared in Example 30 (0.325 mmol, 150 mg) in methanol (5 mL) was added paraformaldehyde (0.813 mmol, 25 mg), Na(OAc)3BH and a catalytic amount of HOAc at room temperature. The resulting mixture was kept stirred at room temperature overnight. Then EtOAc (20 mL) was added to the mixture and the mixture was washed with saturated NaHCO3 and water. The organic layer was dried over Na2SO4 and concentrated to dryness. The crude product was purified through a column of silica gel with a gradient of 0% to 50% MeOH in DCM to afford the title compound 47. 1H NMR (CDCl3): δ 8.21 (d, J=8.1 Hz, 1H), 8.18 (br s, 1H), 8.04 (d, J=8.1 Hz, 1H), 7.87 (dd, J=7.84, 7.86 Hz, 1H), 4.63 (m, 1H), 4.15 (m, 1H), 3.95 (m, 1H), 3.52 (m, 1H), 3.23 (m, 1H), 2.90-2.55 (m, 3H), 2.70 (d, J=5.4 Hz, 3H), 2.07-1.54 (m, 8H), 1.00 (m, 6H), 0.92 (m, 2H), 0.80 (m, 2H). LC: 100%. MS: 490.2 (M+1).

Workup

  1. customat room temperature
  2. washthe mixture was washed with saturated NaHCO3 and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified through a column of silica gel with a gradient of 0% to 50% MeOH in DCM

Sources & evidence

ORD record
ord-3693db6d0eb34cf7a22cb2b3719fab7f
Source dataset
uspto-grants-2015_04
Patent number
US09000174B2

Reaction notes

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