Dichloromethane → HCID 11363767, compound

HRID 2216636Notes

Reaction equation

HRID 2216636 reaction equation
[C:1]([C:4]1[O:8][C:7]([NH:9][C:10](=[O:27])[CH:11]([NH:15][C:16](=[O:26])[CH2:17][C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[CH2:12][CH2:13][CH3:14])=[N:6][CH:5]=1)(=O)[CH3:2].[CH2:28]([NH2:33])[CH2:29][CH:30]([CH3:32])[CH3:31].CC([O-])=O.[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].[BH3-]C#N.[Na+].C(Cl)[Cl:51]>CC(O)=O>[ClH:51].[CH3:31][CH:30]([CH3:32])[CH2:29][CH2:28][NH:33][CH:1]([C:4]1[O:8][C:7]([NH:9][C:10](=[O:27])[CH:11]([NH:15][C:16](=[O:26])[CH2:17][C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[CH2:12][CH2:13][CH3:14])=[N:6][CH:5]=1)[CH3:2]

Participants

8

Reactant 6

HCID 6344DichloromethaneHCID 7894IsoamylamineHCID 24436Sodium SulfateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 11268961HCID 11268961, compound

Product 1

HCID 11363767HCID 11363767, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acid (5-acetyl-oxazol-2-yl)-amide (100 mg, 0.26 mmol), isoamylamine (0.2 ml), NaOAc, Na2SO4, AcOH(0.1 ml) in methylene chloride was stirred at room temperature for 2 hr. NaBH3CN (80 mg, 3.4 mmol) was added. The mixture was heated at 40–45° C. until all starting material was consumed and product was formed. The mixture was quenched with dilute NaOH, extracted with methylene chloride, then extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 (anhydrous), filtered, and concentrated to give 120 mg of the title compound. The crude material was purified by silica gel column chromatography using 1% to 5% MeOH in methylene chloride as eluent to give the desired product that was prepared to the corresponding HCl salt with HCl in dioxane. The salt was titrated with hexane to give the title compound as a white solid. LC-MS, RT=1.3 min, M−1=449.2.

Workup

  1. temperatureThe mixture was heated at 40–45° C. until all starting material
  2. customwas consumed
  3. customproduct was formed
  4. customThe mixture was quenched with dilute NaOH
  5. extractionextracted with methylene chloride
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over Na2SO4 (anhydrous)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bf6308055eb442eb9fa60442e93e7114
Source dataset
uspto-grants-2006_09
Patent number
US07112599B2

Reaction notes

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