(2R)-Oxiran-2-ylmethyl butanoate → HCID 70196442, compound

HRID 1418645Notes

Reaction equation

HRID 1418645 reaction equation
[C:1]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:21][CH:20]([O:22][CH3:23])[CH2:19]2)=[C:14]([F:24])[CH:13]=1)(OCC1C=CC=CC=1)=O.C([Li])CCC.[C:30]([O:35][CH2:36][C@@H:37]1[O:39]C1)(=[O:34])CCC>O1CCCC1>[F:24][C:14]1[CH:13]=[C:12]([N:11]2[CH2:1][C@H:36]([CH2:37][OH:39])[O:35][C:30]2=[O:34])[CH:17]=[CH:16][C:15]=1[N:18]1[CH2:21][CH:20]([O:22][CH3:23])[CH2:19]1

Participants

5

Reactant 3

HCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 54152127HCID 54152127, compoundHCID 178418339Butyllithium

Product 1

HCID 70196442HCID 70196442, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(carbobenzyloxy)-3-fluoro-4-(3-methoxy-1-azetidinyl)aniline (0.865 g, 2.62 mmol) in dry tetrahydrofuran (10 mL) was cooled to -78° C. under a nitrogen atmosphere and treated with n-butyllithium (1.65 mL of a 1.6M solution in hexanes, 2.65 mmol). After stirring at -78°0 C. for 15 min, the reaction mixture was treated with (R)-glycidyl butyrate (0.374 mL, 2.65 mmol). The cooling bath was then removed and the reaction mixture allowed to warm to ambient temperature. After 1 h the reaction was judged complete by TLC analysis. The reaction mixture was quenched by the addition of saturated aqueous ammonium chloride (0.5 mL) and concentrated under reduced pressure to a yellow solid. Chromatography over silica gel (10 g), eluting with a gradient of 1-2% methanol/chloroform afforded, after concentration of appropriate fractions, 0.530 g (68%) of the title compound as an off-white solid with mp 131°-132° C. and MS(EI) 296 (M+).

Workup

  1. customThe cooling bath was then removed
  2. waitAfter 1 h the reaction was judged complete by TLC analysis
  3. customThe reaction mixture was quenched by the addition of saturated aqueous ammonium chloride (0.5 mL)
  4. concentrationconcentrated under reduced pressure to a yellow solid
  5. washChromatography over silica gel (10 g), eluting with a gradient of 1-2% methanol/chloroform
  6. customafforded

Sources & evidence

ORD record
ord-17daece252af4a58b9183f0ea3d91709
Source dataset
uspto-grants-1999_03
Patent number
US05883093

Reaction notes

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