(2R)-Oxiran-2-ylmethyl butanoate → HCID 71182943, compound

HRID 1891400Notes

Reaction equation

HRID 1891400 reaction equation
C([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][CH:21]3[CH2:23][C:24]4([CH2:29][CH:20]3[CH2:19]2)[O:28][CH2:27][CH2:26][O:25]4)=[C:14]([F:30])[CH:13]=1)=[O:10])C1C=CC=CC=1.C([Li])CCC.[C:36](OC[C@@H]1OC1)(=[O:40])[CH2:37][CH2:38]C>O1CCCC1>[F:30][C:14]1[CH:13]=[C:12]([N:11]2[CH2:38][C@H:37]([CH2:36][OH:40])[O:8][C:9]2=[O:10])[CH:17]=[CH:16][C:15]=1[N:18]1[CH2:19][CH:20]2[CH2:29][C:24]3([CH2:23][CH:21]2[CH2:22]1)[O:25][CH2:26][CH2:27][O:28]3

Participants

5

Reactant 3

HCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 71182917HCID 71182917, compoundHCID 178418339Butyllithium

Product 1

HCID 71182943HCID 71182943, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

24.12 g (58.5 mmol) of 2-[4-[[(benzyloxy)carbonyl]amino]-2-fluorophenyl]-hexahydro-1H-spiro[cyclopenta[c]pyrrol-5,2′-[1,3]dioxolane] prepared in the step 6 was dissolved in 250 ml of tetrahydrofuran, the temperature was cooled to −78° C., and 44 ml (70.4 mmol) of 1.6 M n-butyllithium was slowly added over 30 minutes. After the reaction mixture was stirred for 1 hour, 9.11 ml (60.0 mmol) of (−)-(R)-glycidyl butyrate was added dropwise over 30 minutes, and the mixture was stirred for 12 hours while raising the temperature to room temperature. After the reaction was completed, the solvent was removed under reduced pressure, 250 ml of ethyl acetate was added, the mixture was washed with a saturated aqueous solution of ammonium chloride and distilled water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain 21.4 g (97%) of the title compound, of which NMR data is as follows.

Workup

  1. stirringthe mixture was stirred for 12 hours
  2. temperaturewhile raising the temperature to room temperature
  3. customthe solvent was removed under reduced pressure, 250 ml of ethyl acetate
  4. additionwas added
  5. washthe mixture was washed with a saturated aqueous solution of ammonium chloride
  6. distillationdistilled water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ef0fac084d34f73b9dda903e841556e
Source dataset
uspto-grants-2013_08
Patent number
US08507540B2

Reaction notes

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