Triethylamine → HCID 57947489, compound

HRID 409871Notes

Reaction equation

HRID 409871 reaction equation
C1([NH2+]C2CCCCC2)CCCCC1.[CH2:14]([O:21][C:22]([N:24]([CH3:37])[C@@H:25]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:26]([O-])=[O:27])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(CC)CC.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O>[CH2:14]([O:21][C:22]([N:24]([CH3:37])[C@H:25]([CH2:26][OH:27])[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:31])=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 141232704HCID 141232704, compound

Product 1

HCID 57947489HCID 57947489, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (S)-2-((benzyloxycarbonyl)(methyl)amino)-4-tert-butoxy-4-oxobutanoic acid dicyclohexylammonium salt (20 g, 0.0386 mol) and Et3N (7.90 mL, 0.0579 mol) in THF (500 mL) was added isobutyl chloroformate (6.05 mL, 0.0463 mol) at 0° C. The reaction mixture was stirred for 1 h, and filtered to remove TEA salt. To the filtrate was added a solution of NaBH4 (2.19 g, 0.0579 mol) in THF (50 mL) and water (100 mL) at 0-5° C. The reaction mixture was stirred at RT for 1 h and quenched with saturated NH4Cl solution. The reaction mixture was concentrated to remove most of THF and extracted with EtOAc (700 mL×3). The organic layers were washed with water, NaHCO3 and brine, dried over Na2SO4, and concentrated to give (S)-tert-butyl 3-((benzyloxycarbonyl)(methyl)amino)-4-hydroxybutanoate (10 g), which was used without further purification. LRMS (M+Na+) m/z 346.1.

Workup

  1. filtrationfiltered
  2. customto remove TEA salt
  3. stirringThe reaction mixture was stirred at RT for 1 h
  4. customquenched with saturated NH4Cl solution
  5. concentrationThe reaction mixture was concentrated
  6. customto remove most of THF
  7. extractionextracted with EtOAc (700 mL×3)
  8. washThe organic layers were washed with water, NaHCO3 and brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-512767a163384b43852bce9eb1916e98
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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