Triethylamine → 2-(4-{2-[(2,4-Difluorobenzyl)(heptyl)amino]-2-oxoethoxy}-3-methoxyphenyl)ethyl methanesulfonate

HRID 898896Notes

Reaction equation

HRID 898896 reaction equation
[F:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[CH2:4][N:5]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][C:10]=1[O:18][CH3:19].C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[CH3:40][S:41]([O:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([N:5]([CH2:4][C:3]2[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:2]=2[F:1])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:20])=[C:10]([O:18][CH3:19])[CH:11]=1)(=[O:43])=[O:42]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 69258529N-(2,4-difluorobenzyl)-N-heptyl-2-[4-(2-hydroxyethyl)-2-methoxyphenoxy]acetamide

Product 1

HCID 866009662-(4-{2-[(2,4-Difluorobenzyl)(heptyl)amino]-2-oxoethoxy}-3-methoxyphenyl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2,4-difluorobenzyl)-N-heptyl-2-[4-(2-hydroxyethyl)-2-methoxyphenoxy]acetamide (A)(132 mg, 0.294 mmol) was dissolved in DCM (10 ml). It was cooled in an ice-bath. Triethylamine (0.05 ml, 0.352 mmol) was added and then methanesulfonyl chloride (37 mg, 0.323 mmol) was dropped in. The cooling-bath was removed after 30 minutes. The mixture was stirred at room temperature overnight. LS-MS showed that ca 50% of A was not reacted. The mixture was cooled in an ice-bath and 0.05 ml of triethylamine was added, followed by 0.025 ml of methanesulfonyl chloride. After addition, the cooling-bath was removed and the mixture was stirred for 5 hours more. It was then washed with water (×2) and brine, dried (magnesium sulphate) and evaporated. Oil product 138 mg was left and used for next step without further purification.

Workup

  1. temperatureIt was cooled in an ice-bath
  2. customThe cooling-bath was removed after 30 minutes
  3. customwas not reacted
  4. temperatureThe mixture was cooled in an ice-bath
  5. additionAfter addition
  6. customthe cooling-bath was removed
  7. stirringthe mixture was stirred for 5 hours more
  8. washIt was then washed with water (×2) and brine
  9. dry with materialdried (magnesium sulphate)
  10. customevaporated
  11. waitOil product 138 mg was left
  12. customused for next step without further purification

Sources & evidence

ORD record
ord-eb3ca7325a87433ba1f194ff4f28f37b
Source dataset
uspto-grants-2008_04
Patent number
US07351858B2

Reaction notes

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