Allyl bromide → 3-Allyloxy-N-[(1S,2S,4R)-1-benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-5-(2-oxopyrrolidin-1-yl)-benzamide

HRID 1612476Notes

Reaction equation

HRID 1612476 reaction equation
[CH2:1]([C@H:8]([NH:23][C:24](=[O:38])[C:25]1[CH:30]=[C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2=[O:36])[CH:28]=[C:27]([OH:37])[CH:26]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:45](Br)[CH:46]=[CH2:47]>CN(C=O)C.C(OCC)(=O)C.Cl>[CH2:47]([O:37][C:27]1[CH:26]=[C:25]([CH:30]=[C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2=[O:36])[CH:28]=1)[C:24]([NH:23][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]([OH:22])[CH2:10][C@H:11]([C:13](=[O:21])[NH:14][CH2:15][CH2:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH3:12])=[O:38])[CH:46]=[CH2:45]

Participants

7

Reactant 3

HCID 7841Allyl bromide2×HCID 10796Cesium carbonateHCID 10218066N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-hydroxy-5-(2-oxopyrrolidin-1-yl)-benzamide

Product 1

HCID 101965983-Allyloxy-N-[(1S,2S,4R)-1-benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-5-(2-oxopyrrolidin-1-yl)-benzamide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[(1S,2S,4R)-1-Benzyl-4-(3,3-bimethylbutylcarbamoyl)-2-hydroxypentyl]-3-hydroxy-5-(2-oxopyrrolidin-1-yl)-benzamide (E2) (0.061 g, 0.117 mmol), caesium carbonate (0.050 g, 0.152 mmol) and allyl bromide (0.016 ml, 0.176 mmol) in DMF (1 ml) was stirred vigorously at room temperature for 2 hrs. More allyl bromide (0.008 ml) was added and stirring was continued for a further 1 hr. The mixture was diluted with ethyl acetate and 2N HCl and the product was extracted into ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate and evaporated. Purification by column chromatography on silica gel (elution with 2–5% methanol in dichloromethane) gave the product, 0.047 g.

Workup

  1. stirringstirring
  2. waitwas continued for a further 1 hr
  3. extractionthe product was extracted into ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customPurification by column chromatography on silica gel (elution with 2–5% methanol in dichloromethane)
  8. customgave the product, 0.047 g

Sources & evidence

ORD record
ord-ccec4503197c431f984706db1c432270
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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