Triethylamine → HCID 86714592, compound

HRID 1025933Notes

Reaction equation

HRID 1025933 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:18])([CH2:16][F:17])[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.O>[F:17][CH2:16][C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:18])[CH2:13][OH:14]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 86714593HCID 86714593, compound

Product 1

HCID 86714592HCID 86714592, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(benzyloxycarbonylamino)-3-fluoro-2-methylpropanoic acid (1.1 g, 4.9 mmol) in THF (16 ml) was cooled to 0° C., and triethylamine (518 mg, 6.1 mmol) was added, then ethyl chloroformate (663 mg, 6.11 mmol). A solution of sodium borohydride (370 mg, 9.8 mmol) in water (4 ml) was added, and the reaction warmed to RT over 4 h. The reaction was quenched with 1 M HCl, and extracted with EtOAc. The organic layers were combined, washed with sat. NaCl, dried on Na2SO4, and concentrated in vacuo. Flash chromatography (0% to 10% MeOH in DCM) afforded the title compound as a clear oil (915 mg, 77%). 1H NMR (CDCl3, 400 MHz) δ 1.31 (s, 3H), 3.4 (br s, 1H), 3.72-3.80 (m, 2H) 4.47 (dd, J=9.6, 18.4 Hz, 1H), 4.60 (dd, J=9.2, 18.8 Hz, 1H), 5.12 (s, 2H), 5.32 (s, 1H), 7.28-7.37 (m, 5H). 19F NMR (CDCl3, 376 MHz) δ −231.2 (t, J=48.9 Hz). 13C NMR (CDCl3, 100 MHz) δ 19.2 (d, J=4 Hz), 56.8 (d, J=17 Hz), 66.4 (d, J=4 Hz), 66.9, 85 (d, J=173 Hz), 128.1, 128.3, 128.6, 128.6, 136.0, 156.0.

Workup

  1. customThe reaction was quenched with 1 M HCl
  2. extractionextracted with EtOAc
  3. washwashed with sat. NaCl
  4. customdried on Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95bb4deefa534aa2a88035037a60de8f
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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