Acetic Acid → HCID 131731932, compound

HRID 61495Notes

Reaction equation

HRID 61495 reaction equation
O[C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:4]([C:15]([O:17][CH3:18])=[O:16])[CH2:3]1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.[C:23](O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:19]1([NH:22][CH2:23][CH:2]2[CH2:7][CH2:6][C@H:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:4]([C:15]([O:17][CH3:18])=[O:16])[CH2:3]2)[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 86621492HCID 86621492, compound

Product 1

HCID 131731932HCID 131731932, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 250, Part 4 (174 mg, 0.644 mmol) and cyclopropylamine (35.6 mg, 0.611 mmol) were dissolved in methanol (6.0 mL). That solution was treated with acetic acid (0.209 mL) and sodium cyanoborohydride (38.4 mg, 0.611 mmol). The reaction mixture was stirred at rt overnight. It was concentrated, diluted with ethyl acetate and washed with a saturated NaHCO3 solution. The organic layer was dried over MgSO4, filtered and concentrated. The residue was flash chromatographed (silica, 5% to 6% to 10% MeOH/CH2Cl2) to provide the desired product as a colorless oil (131 mg, 68.8% yield). LCMS: m/z 312.2 (M+H)+.

Workup

  1. concentrationIt was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with a saturated NaHCO3 solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed (silica, 5% to 6% to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9b389c1506e94291b99d500c3e0a0ca8
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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