Benzyl Bromide → HCID 86716590, compound

HRID 929902Notes

Reaction equation

HRID 929902 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([NH:16][C@@:17]1([C:27]([OH:29])=[O:28])[CH2:22][C:21](=[O:23])[C@@H:20]2[C@H:18]1[C@H:19]2[C:24]([OH:26])=[O:25])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:9]([O:13][C:14]([NH:16][C@@:17]1([C:27]([O:29][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:28])[CH2:22][C:21](=[O:23])[C@@H:20]2[C@H:18]1[C@H:19]2[C:24]([O:26][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:25])=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 58319586HCID 58319586, compound

Product 1

HCID 86716590HCID 86716590, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add benzyl bromide (8.69 mL, 72.9 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 (7.27 g, 24.3 mmol) and cesium carbonate (15.83 g, 48.6 mmol) in dry N,N-dimethylformamide (60 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 gummy yellow foam (9.15 g, 78.5%). MS (m/z): 502 (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-1b4bea395bc440a792a5fb88edf07d0b
Source dataset
uspto-grants-2016_03
Patent number
US09296710B2

Reaction notes

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