Hydrochloric Acid → O-(4-fluorophenyl)-L-homoserine ethyl ester hydrochloride

HRID 1612091Notes

Reaction equation

HRID 1612091 reaction equation
[C:1]([O:5][C:6](=[O:19])[C@H:7]([CH2:16][CH2:17][OH:18])[NH:8]C(OC(C)(C)C)=O)([CH3:4])(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:39][C:40]1[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=1.N(C(N(C)C)=O)=NC(N(C)C)=O.[ClH:59]>O1CCCC1.C(O)C>[ClH:59].[CH2:1]([O:5][C:6](=[O:19])[C@H:7]([CH2:16][CH2:17][O:18][C:43]1[CH:44]=[CH:45][C:40]([F:39])=[CH:41][CH:42]=1)[NH2:8])[CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 11054918(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

Product 1

HCID 68613683O-(4-fluorophenyl)-L-homoserine ethyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of BOC-L-homoserine t-butyl ester (3.2 g, 11.6 mmol) in tetrahydrofuran is added triphenylphosphine (7.59 g, 29 mmol), p-fluorophenol (2.08 g, 18.6 mmol) and 1,1′-azobis(N,N-dimethylformamide) (3.2 g, 18.6 mmol). The mixture is stirred overnight, washed with brine, dried over MgSO4, and the solvent is removed to give an orange oil. The oil is purified by flash chromatography (SiO2, 85% hexane/15% ethyl acetate) to give a clear oil which is dissolved in ethanol (100 mL) and the solution is saturated with HCl gas, then stirred overnight. The mixture is concentrated to give O-(4-fluorophenyl)-L-homoserine ethyl ester hydrochloride as a white solid.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. customthe solvent is removed
  4. customto give an orange oil
  5. customThe oil is purified by flash chromatography (SiO2, 85% hexane/15% ethyl acetate)
  6. customto give a clear oil which
  7. stirringstirred overnight
  8. concentrationThe mixture is concentrated

Sources & evidence

ORD record
ord-6aa75c5809fb4a59b63dcb321403db6c
Source dataset
uspto-grants-2006_01
Patent number
US06992105B2

Reaction notes

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