Benzyl Bromide → HCID 10282284, compound

HRID 1071007Notes

Reaction equation

HRID 1071007 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C@H](C(O)=O)CC1[CH:21]=[C:20]2[C:15](C=CC=[CH:19]2)=CC=1.[CH2:25]([C@@H:32]1[C@@H:40]([OH:41])[C@H:39]([CH3:42])[O:38][C:37](=[O:43])[C@@H:36]([NH:44][C:45]([C:47]2[C:52]([OH:53])=[C:51]([O:54][CH3:55])[CH:50]=[CH:49][N:48]=2)=[O:46])[CH2:35][O:34][C:33]1=[O:56])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=[O:58].[K+].[K+]>CC(C)=O.CCOC(C)=O>[CH3:15][CH:20]([CH3:19])[C:21]([O:41][C@@H:40]1[C@@H:32]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:33](=[O:56])[O:34][CH2:35][C@H:36]([NH:44][C:45]([C:47]2[C:52]([O:53][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:51]([O:54][CH3:55])[CH:50]=[CH:49][N:48]=2)=[O:46])[C:37](=[O:43])[O:38][C@H:39]1[CH3:42])=[O:58]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1859152-NaphthylalanineHCID 11236123N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide

Product 1

HCID 10282284HCID 10282284, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl bromide (23.5 mL) was added to a solution of Nal (11.3 mol, 1.68 g) in acetone (60 mL). Compound 1 (22.5 mmol, 10 g) was added followed by powdered K2CO3.(38.8 mol, 5.3 g) and the mixture stirred vigorously overnight. The mixture was diluted with EtOAc (150 mL) and washed with H2O (2×150 mL). The organic layer was dried (MgSO4), and concentrated in vacuo. Purification via column chromatography (acetone/hexanes) gave 4.70 g (39%) of Compound 2 as an off-white solid. 1H-NMR and MS (M+1)+=535 were consistent for Compound 2.

Workup

  1. washwashed with H2O (2×150 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification via column chromatography (acetone/hexanes)

Sources & evidence

ORD record
ord-9b50d8346d7e4d33857678b75d69e0ae
Source dataset
uspto-grants-2005_06
Patent number
US06903219B2

Reaction notes

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