Triethylamine → HCID 57947489, compound

HRID 341008Notes

Reaction equation

HRID 341008 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:24])[C@@H:12]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O>[CH2:1]([O:8][C:9]([N:11]([CH3:24])[C@H:12]([CH2:13][OH:14])[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 7019794HCID 7019794, compound

Product 1

HCID 57947489HCID 57947489, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (S)-2-((benzyloxycarbonyl)(methyl)amino)-4-tert-butoxy-4-oxobutanoic acid dicyclohexylamimonium 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-6e9ff38b74ec411db9f2d796d08f2e1c
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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