(2R)-Oxiran-2-ylmethyl butanoate → HCID 67274100, compound

HRID 1163355Notes

Reaction equation

HRID 1163355 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](OCC3C=CC=CC=3)=O)=[CH:20][C:19]=2[F:35])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36]([O:41][CH2:42][C@@H:43]1[O:45]C1)(=[O:40])CCC>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:25][C@H:42]([CH2:43][OH:45])[O:41][C:36]3=[O:40])=[CH:20][C:19]=2[F:35])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 67273732HCID 67273732, compound

Product 1

HCID 67274100HCID 67274100, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.6 g (15 mmol) 4-(4-benzyloxycarbonylamino-2-fluoro-phenylamino)-piperidine-1-carboxylic acid benzyl ester in 50 ml THF at −78° C. was added dropwise 12.12 ml nBuli 1.6 M (19.5 mmol). The mixture was further stirred at this temperature for 10 min. The resulting yellow solution was allowed to reach −40° C. over 10 min. 3.0 ml (21 mmol) of (R)-glycidyl butyrate was then added and the solution was allowed to reach slowly RT and further stirred for 16 h. The reaction was quenched with a saturated ammonium chloride solution, diluted with 400 ml of EtOAc. The organic layer was washed with water and brine, dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography using a CH2Cl2/MeOH 5% mixture.

Workup

  1. waitto reach −40° C. over 10 min
  2. customto reach slowly RT
  3. stirringfurther stirred for 16 h
  4. customThe reaction was quenched with a saturated ammonium chloride solution
  5. additiondiluted with 400 ml of EtOAc
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-6ae491643b7740e28fee10f39574a2ce
Source dataset
uspto-grants-2010_10
Patent number
US07820823B2

Reaction notes

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