Cesium carbonate → HCID 58319579, compound

HRID 1879577Notes

Reaction equation

HRID 1879577 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[C:10]([O:14][C:15]([NH:17][C@@:18]1([C:28]([OH:30])=[O:29])[CH2:23][C:22](=[O:24])[C@@H:21]2[C@H:19]1[C@H:20]2[C:25]([OH:27])=[O:26])=[O:16])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:29][C:28]([C@:18]1([NH:17][C:15]([O:14][C:10]([CH3:13])([CH3:11])[CH3:12])=[O:16])[CH2:23][C:22](=[O:24])[C@@H:21]2[C@H:19]1[C@H:20]2[C:25]([O:27][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[F:1])=[O:26])=[O:30]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 58319586HCID 58319586, compound

Product 1

HCID 58319579HCID 58319579, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 2-fluorobenzyl bromide (0.21 mL, 1.7 mmol) dropwise to a stirred suspension of (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (0.17 g, 0.57 mmol) and cesium carbonate (0.37 g, 1.14 mmol) in dry N,N-dimethylformamide (1.42 mL). Stir the resulting mixture at room temperature overnight under nitrogen. Quench with water and dilute with ethyl acetate. Extract the aqueous phase with ethyl acetate (3 times) and wash the organic layers with brine and water. Dry over sodium sulfate, filter and concentrate to give the crude material as a pale brown oil. Purify by flash chromatography eluting with ethyl acetate:hexane (20:80 to 30:70) to give the title compound as a pale yellow oil (229 mg, 79%). MS (m/z): 538 (M+23).

Workup

  1. customQuench with water
  2. additiondilute with ethyl acetate
  3. extractionExtract the aqueous phase with ethyl acetate (3 times)
  4. washwash the organic layers with brine and water
  5. dry with materialDry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto give the crude material as a pale brown oil
  9. customPurify by flash chromatography
  10. washeluting with ethyl acetate:hexane (20:80 to 30:70)

Sources & evidence

ORD record
ord-7f8e27df8f9343e492faf0089937275c
Source dataset
uspto-grants-2012_11
Patent number
US08318184B2

Reaction notes

Loading…