Triethylamine → HCID 68453549, compound

HRID 2358417Notes

Reaction equation

HRID 2358417 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[C:12]([NH2:17])=[CH:11][C:10]=1[O:18][CH3:19])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[C:12]([NH:17][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:11][C:10]=1[O:18][CH3:19])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68456961HCID 68456961, compound

Product 1

HCID 68453549HCID 68453549, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a ice-cooled solution of (4-amino-2-methoxy-5-vinyl-benzyl)-carbamic acid tert-butyl ester (220 mg, 0.79 mmol) in methylene chloride was added triethylamine (132 L) followed by methanesulfonyl chloride (72 L). The mixture was warmed up to room temperature and stirred for 4 hrs. The reaction was quenched with water, and the reaction solution was extracted with methylenechloride, washed with water and brine, dried over anhyd. MgSO4, filtered and concentrated under reduced pressure. The resulting residue was treated with 1N NaOH/MeOH/THF (1/2/1) for 2 hrs, and then neutralized by adding 1N HCl. After evaporating methanol, water was added to the residue. The resulting mixture was extracted with EtOAc, and the combined organic layer was washed with brine, dried over anhyd. MgSO4, filtered, and concentrated under reduced pressure. The crude residue was column-chromatographed (hexane/ethylacetate=1/1) to yield a white solid (260 mg, 92%).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe reaction solution was extracted with methylenechloride
  3. washwashed with water and brine
  4. customdried over anhyd
  5. filtrationMgSO4, filtered
  6. concentrationconcentrated under reduced pressure
  7. additionThe resulting residue was treated with 1N NaOH/MeOH/THF (1/2/1) for 2 hrs
  8. additionby adding 1N HCl
  9. customAfter evaporating methanol, water
  10. additionwas added to the residue
  11. extractionThe resulting mixture was extracted with EtOAc
  12. washthe combined organic layer was washed with brine
  13. customdried over anhyd
  14. filtrationMgSO4, filtered
  15. concentrationconcentrated under reduced pressure
  16. customThe crude residue was column-chromatographed (hexane/ethylacetate=1/1)

Sources & evidence

ORD record
ord-4b1669f3ff3a4c4d9da059990a8a45d7
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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