Triethylamine → HCID 178505322, compound

HRID 1672717Notes

Reaction equation

HRID 1672717 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[C:27]([Cl:29])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([C@H:19]3[CH2:24][CH2:23][C@H:22]([OH:25])[CH2:21][CH2:20]3)[C:15]2=[O:26])=[C:11]([Cl:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Cl:30])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([C@H:19]3[CH2:20][CH2:21][C@H:22]([O:25][S:39]([CH3:38])(=[O:41])=[O:40])[CH2:23][CH2:24]3)[C:15]2=[O:26])=[C:27]([Cl:29])[CH:28]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178516684HCID 178516684, compound

Product 1

HCID 178505322HCID 178505322, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (R)-3-(4-Benzyloxy-2,6-dichloro-benzyl)-trans-1-(4-hydroxy-cyclohexyl)-pyrrolidin-2-one (1.291 g, 2.86 mmol) in 25 ml of dry dichloromethane at 0° C. Add triethylamine (0.73 ml, 5.77 mmol) followed by methanesulfonyl chloride (0.25 ml, 3.17 mmol). Stir at room temperature for 3 hours. Quench with 1N HCl and extract with ethyl acetate. Wash the extract with 1N HCl, NaHCO3 and brine. Dry over magnesium sulfate, filter, and concentrate. Purify by column chromatography to receive 1.315 g of the title compound: Mass spectrum (apci) m/z=526 (M+H).

Workup

  1. customQuench with 1N HCl
  2. extractionextract with ethyl acetate
  3. washWash the
  4. extractionextract with 1N HCl, NaHCO3 and brine
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify by column chromatography

Sources & evidence

ORD record
ord-c5da05fb69454325982d53e847214eb1
Source dataset
uspto-grants-2011_08
Patent number
US07998999B2

Reaction notes

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