Anisole → HCID 86757153, compound

HRID 1385048Notes

Reaction equation

HRID 1385048 reaction equation
COC1C=CC(C[S:8][C@@H:9]([CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:44]([C:46]2[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=2)=[O:45])[C:10]([NH:12][C@@:13]2([CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:17][CH2:16][N:15]([C@H:18]([C:26](=[O:29])[NH:27][CH3:28])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]2=[O:30])=[O:11])=CC=1.C1(OC)C=CC=CC=1>ClCCl>[SH:8][C@@H:9]([CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:44]([C:46]1[CH:51]=[CH:50][N:49]=[CH:48][CH:47]=1)=[O:45])[C:10]([NH:12][C@@:13]1([CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:17][CH2:16][N:15]([C@H:18]([C:26](=[O:29])[NH:27][CH3:28])[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]1=[O:30])=[O:11]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 69947169HCID 69947169, compound

Product 1

HCID 86757153HCID 86757153, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine (S)-3-((S)-2-(p-methoxybenzylthio)-6-(pyrid-4-ylcarbonylamino)hexamido)-3-phenethyl-1-((S)-1-methylcarbamoyl-2-phenylethyl)pyrrolidin-2-one (122 mg, 0.166 mmol), mercuric acetate (66 mg, 0.207 mmol), and anisole (0.18 mL, 1.7 mmol) in dichloromethane (5 mL). Cool in an ice bath and degas by repeated cycles of vacuum and filling with nitrogen. Add trifluoroacetic acid (2 mL). After 3 hours, bubble hydrogen disulfide gas through the reaction mixture for about 15 minutes to give a black precipitate. Remove the precipitate by filtration and rise with dichloromethane. Evaporate the filtrate in vacuo and remove residual trifluoroacetic acid by coevaporation with carbon tetrachloride to give a residue. Triturate the residue sequentially with hexane, diethyl ether, and then hexane to give the title compound as a solid (102 mg, 84%). 13C NMR (CDCl3) d 24.4, 26.5, 27.6, 29.4, 33.9, 35.2, 36.9, 39.8, 42.0, 46.2, 61.7, 61.9, 123.8, 126.8, 126.9, 128.3, 128.6, 128.86, 128.93, 137.7, 140.2, 145.1, 147.0, 163.6, 169.3, 173.0, 173.5. MS Calculated for C34H41N5O4S.C2HF3O2=615.8.114.0. Found (M+H)+=616.

Workup

  1. temperatureCool in an ice bath
  2. customdegas by repeated cycles of vacuum
  3. custombubble hydrogen disulfide gas through the reaction mixture for about 15 minutes
  4. customto give a black precipitate
  5. customRemove the precipitate
  6. filtrationby filtration and rise with dichloromethane
  7. customEvaporate the filtrate in vacuo
  8. customremove residual trifluoroacetic acid by coevaporation with carbon tetrachloride
  9. customto give a residue
  10. customTriturate the residue sequentially with hexane, diethyl ether

Sources & evidence

ORD record
ord-4e3281841f794053b267abdde711d26a
Source dataset
uspto-grants-2001_07
Patent number
US06262080B1

Reaction notes

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