Potassium Carbonate → Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}-L-glutamate

HRID 591284Notes

Reaction equation

HRID 591284 reaction equation
[F:1][CH2:2][CH2:3]I.C(=O)([O-])[O-].[K+].[K+].[C:11]([O:15][C:16]([NH:18][C@H:19]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:20][C@H:21]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][N:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C)C=O>[C:11]([O:15][C:16]([NH:18][C@H:19]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:20][C@H:21]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:3][CH2:2][F:1])=[CH:32][N:31]=1)[C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[O:17])([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 70957058Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[(5-hydroxypyridin-2-yl)methyl]-L-glutamate

Product 1

HCID 70674548Di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}-L-glutamateYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 196 mg 1-fluoro-2-iodoethane (1.13 mmol) in N,N-dimethylformamide (25 mL) was subsequently added 363 mg potassium carbonate (2.63 mmol), followed by 350 mg di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-[(5-hydroxypyridin-2-yl)methyl]-L-glutamate 0.75 mmol), and the resulting mixture was stirred for 4 h at room temperature. The mixture was than partitioned between water and dichloromethane, and the organic layer was washed with brine, dried over magnesium sulfate, and evaporated. Purification of the crude product by preparative HPLC (method A) gave 313 mg of the target compound (81% yield).

Workup

  1. customthan partitioned between water and dichloromethane
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customPurification of the crude product by preparative HPLC (method A)

Sources & evidence

ORD record
ord-d90f8d72f99041f787ac760f5765461a
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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