Triethylamine → HCID 178454001, compound

HRID 2089037Notes

Reaction equation

HRID 2089037 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]2)[CH:5]=[C:4]([I:16])[CH:3]=1.C(N(CC)CC)C.[O:24](C(OC(C)(C)C)=O)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=O>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:10][CH2:11][C@H:12]([NH:15][C:25](=[O:24])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:13][CH2:14]2)[CH:5]=[C:4]([I:16])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 178511613HCID 178511613, compound

Product 1

HCID 178454001HCID 178454001, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of Example 213a (7.00 g, 19.91 mmol) and triethylamine (3.61 mL, 25.9 mmol) in tetrahydrofuran (150 mL) was added BOC2O (5.08 mL, 21.90 mmol) at 0° C. The ice bath was removed and the reaction mixture was stirred at room temperature for 90 minutes. The reaction mixture was diluted with EtOAc and washed with brine and saturated sodium bicarbonate. The organic layer was dried over MgSO4, filtered, concentrated, and purified on a 150 g column using the ISCO Companion flash system eluting with hexane/EtOAc (8:2 to 6:4) to give 5.42 g of the title compound.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction mixture was diluted with EtOAc
  3. washwashed with brine and saturated sodium bicarbonate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on a 150 g column
  8. washeluting with hexane/EtOAc (8:2 to 6:4)

Sources & evidence

ORD record
ord-dd98400b221c44d5af533a83580beea0
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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