Water → Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)pyridin-2-yl]methyl}-L-glutamate

HRID 591302Notes

Reaction equation

HRID 591302 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][N:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:40]1([CH3:63])[CH:45]=[CH:44][C:43]([S:46]([O:49][CH2:50][CH2:51]OS(C2C=CC(C)=CC=2)(=O)=O)(=[O:48])=[O:47])=[CH:42][CH:41]=1.O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:51][CH2:50][O:49][S:46]([C:43]2[CH:44]=[CH:45][C:40]([CH3:63])=[CH:41][CH:42]=2)(=[O:48])=[O:47])=[CH:22][N:21]=1)[C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 228289Ethylene glycol ditosylateHCID 70957058Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[(5-hydroxypyridin-2-yl)methyl]-L-glutamate

Product 1

HCID 70675125Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)pyridin-2-yl]methyl}-L-glutamateYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 150 mg di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-[(5-hydroxypyridin-2-yl)methyl]-L-glutamate (0.32 mmol) in N,N-dimethylformamide (8 mL) was added 126 mg of cesium carbonate (0.39 mmol), followed by 143 mg of 1,2-ethanediol di-p-toluenesulfonate (0.39 mmol). The mixture was stirred for 5 h at room temperature. Water was added, the mixture was extracted with dichloromethane, and the organic layer was washed with brine, dried over magnesium sulfate, and evaporated. The crude product was purified by preparative HPLC (method A) to give 86 mg (40% yield) of the title compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe crude product was purified by preparative HPLC (method A)

Sources & evidence

ORD record
ord-12a5a13a70764d95b3deb4f4ea9d912a
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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