Ammonium Chloride → acrylic acid (S)-6-[4-[2-(hydroxydinaphthalen-2-ylmethyl)pyrrolidine-1-carbonyl]phenoxy]hexyl ester

HRID 413608Notes

Reaction equation

HRID 413608 reaction equation
S(Cl)(C)(=O)=O.[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1)(=[O:9])[CH:7]=[CH2:8].[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[C:37]([C:44]1[CH:53]=[CH:52][C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=1)([C@@H:39]1[CH2:43][CH2:42][CH2:41][NH:40]1)[OH:38].[NH4+].[Cl-]>C1COCC1.C(N(CC)CC)C>[OH:38][C:37]([C:28]1[CH:29]=[CH:30][C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=1)([C:44]1[CH:53]=[CH:52][C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=1)[C@@H:39]1[CH2:43][CH2:42][CH2:41][N:40]1[C:22]([C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:6](=[O:9])[CH:7]=[CH2:8])=[CH:26][CH:25]=1)=[O:24]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 2733810(S)-Di(naphthalen-2-yl)(pyrrolidin-2-yl)methanolHCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acid

Product 1

HCID 59064084acrylic acid (S)-6-[4-[2-(hydroxydinaphthalen-2-ylmethyl)pyrrolidine-1-carbonyl]phenoxy]hexyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of mesyl chloride (0.1 ml) in 1 ml of dry THF is added dropwise under argon over a period of 15 minutes to a cooled (−20° C.) solution of 4-(6-acryloyloxyhexyloxy)benzoic acid (0.38 g) and triethylamine (0.52 ml) in 10 ml of dry THF. The obtained reaction mixture is stirred for 60 min at −20° C. then treated with a solution of (S)-dinaphthalen-2-ylpyrrolidin-2-ylmethanol (0.46 g) in 5 ml of dry THF and further stirred at −20° C. for 2 h. The reaction mixture is then allowed to warm to room temperature, and stirring is continued overnight. The reaction mixture is then poured into 40 ml of saturated NH4Cl solution and extracted with 4×40 ml of diethyl ether and 20 ml of dichloromethane. The combined organic extracts are washed with saturated NaCl solution (2×80 ml), dried over MgSO4, filtered and evaporated to give a brownish residue. This was purified by chromatography over a short silica column (CH2Cl2 / Et2O : 19 / 1 ) to give acrylic acid (S)-6-[4-[2-(hydroxydinaphthalen-2-ylmethyl)pyrrolidine-1-carbonyl]phenoxy]hexyl ester as a white crystalline material. Yield 0.51 g.

Workup

  1. customThe obtained reaction mixture
  2. stirringfurther stirred at −20° C. for 2 h
  3. temperatureto warm to room temperature
  4. stirringstirring
  5. waitis continued overnight
  6. extractionextracted with 4×40 ml of diethyl ether and 20 ml of dichloromethane
  7. washThe combined organic extracts are washed with saturated NaCl solution (2×80 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customto give a brownish residue
  12. customThis was purified by chromatography over a short silica column (CH2Cl2 / Et2O : 19 / 1 )

Sources & evidence

ORD record
ord-fe11548d0b0b4033beeafd94165b0d1f
Source dataset
uspto-grants-2003_05
Patent number
US06569356B1

Reaction notes

Loading…