Potassium Carbonate → Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[4-(2-fluoroethoxy)benzyl]-hexanedioate

HRID 591276Notes

Reaction equation

HRID 591276 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][CH: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:39]=[CH:40][C:41]([O:44][CH2:3][CH2:2][F:1])=[CH:42][CH:43]=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 70957101Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(4-hydroxybenzyl)hexanedioate

Product 1

HCID 70674547Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[4-(2-fluoroethoxy)benzyl]-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 di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(4-hydroxybenzyl)-hexanedioate (from example 12d; 0.21 mmol), and the resulting mixture was stirred for 4 h at room temperature. The mixture was then partitioned between water and ethyl acetate, the aqueous layer was than 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 85 mg (62% purity adjusted yield) of the target compound in approx. 80% purity.

Workup

  1. customThe mixture was then partitioned between water and ethyl acetate
  2. extractionthan 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. custom85 mg (62% purity adjusted yield) of the target compound in approx. 80% purity

Sources & evidence

ORD record
ord-20b97811b0cf4a1aa94be980484668ed
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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