Acetic Acid → HCID 178452603, compound

HRID 1509185Notes

Reaction equation

HRID 1509185 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][C:21]([NH2:30])=[C:20]([OH:31])[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[O:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[C:1]([O:5][C:6](=[O:32])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][C:21]([NH:30][CH:36]4[CH2:37][CH2:38][O:33][CH2:34][CH2:35]4)=[C:20]([OH:31])[N:19]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178452604HCID 178452604, compound

Product 1

HCID 178452603HCID 178452603, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of tert-butyl(1-(4-(5-amino-6-hydroxy-3-phenylpyridin-2-yl)phenyl)cyclobutyl)carbamate (200 mg, 0.46 mmol) in dry DCE (2 ml) was added dihydro-2H-pyran-4(3H)-one (88 mg, 0.88 mmol), AcOH (0.16 ml, 2.78 mmol), sodium triacetoxyborohydride (275 mg, 1.30 mmol) under nitrogen. The resulting mixture was stirred for 3 h at room temperature. A saturated solution of NaHCO3 was added and the mixture was extracted with AcOEt (3×10 ml). The combined organic phases were dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting residue was used in the next step without any purification.

Workup

  1. extractionthe mixture was extracted with AcOEt (3×10 ml)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe resulting residue was used in the next step without any purification

Sources & evidence

ORD record
ord-b9d5e88a5a7a4748961a0a9336bd6606
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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