Dimethylformamide → HCID 19011475, compound

HRID 1729324Notes

Reaction equation

HRID 1729324 reaction equation
[C:1]([NH:8][C:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CO.O>[CH2:38]([O:11][C:10](=[O:12])[C:9]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 10832046HCID 10832046, compound

Product 1

HCID 19011475HCID 19011475, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

BOC-2,2-dibenzyl glycine (3.29 g, 9.25 mmol) is dissolved in a solution of methanol(18 ml) and water (2 ml) and the pH adjusted to 8 with 20% cesium carbonate solution (11 ml). The solution is concentrated in vacuo to dryness and the residue dissolved in dimethylformamide (DMF) (25 ml) and re-concentrated twice and dried under high vacuum. The cesium salt is taken up into DMF (25 ml), benzyl bromide (1.74 g, 10.2 mmol) is added and the mixture stirred at room temperature for 16 hours. The mixture is concentrated in vacuo and the residue diluted with ether. The organic phase is washed with water, brine, dried over magnesium sulfate, and concentrated in vacuo. The crude product is purified by flash chromatography, eluting with 10% ethyl acetate in hexane to give BOC-2,2-dibenzyl glycine benzyl ester.

Workup

  1. concentrationThe solution is concentrated in vacuo to dryness
  2. dissolutionthe residue dissolved in dimethylformamide (DMF) (25 ml)
  3. concentrationre-concentrated twice
  4. customdried under high vacuum
  5. additionis added
  6. concentrationThe mixture is concentrated in vacuo
  7. additionthe residue diluted with ether
  8. washThe organic phase is washed with water, brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe crude product is purified by flash chromatography
  12. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d9dd0a29712d49ef8aa5655b5bc27988
Source dataset
uspto-grants-1994_07
Patent number
US05332726

Reaction notes

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