Potassium Carbonate → Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}hexanedioate

HRID 591306Notes

Reaction equation

HRID 591306 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]([CH2:27][CH2:28][CH:29]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][N:39]=1)[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C)C=O>[C:11]([O:15][C:16]([NH:18][C@@H:19]([CH2:27][CH2:28][CH:29]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:3][CH2:2][F:1])=[CH:40][N:39]=1)[C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])=[O:17])([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 117812674Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[(5-hydroxypyridin-2-yl)methyl]hexanedioate

Product 1

HCID 117812665Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-{[5-(2-fluoroethoxy)pyridin-2-yl]methyl}hexanedioate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 54 mg 1-fluoro-2-iodoethane (0.31 mmol) in N,N-dimethylformamide (10 mL) was subsequently added 101 mg potassium carbonate (0.73 mmol), followed by 100 mg of di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[(5-hydroxypyridin-2-yl)methyl]hexanedioate (0.21 mmol), and the resulting mixture was stirred for 20 h at room temperature. The mixture was then partitioned between water and ethyl acetate, the aqueous layer was then extracted with ethyl acetate again. The combined organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by preparative HPLC, method A to give 56 mg (approx. 90% purity, 46% purity adjusted yield) of the target compound.

Workup

  1. customThe mixture was then partitioned between water and ethyl acetate
  2. extractionthe aqueous layer was then extracted with ethyl acetate again
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by preparative HPLC, method A
  7. customto give
  8. custom56 mg (approx. 90% purity, 46% purity adjusted yield) of the target compound

Sources & evidence

ORD record
ord-1034ef29596d4d26b75f7559da83f8a7
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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