HCID 67217834, compound → HCID 67444663, compound

HRID 1666979Notes

Reaction equation

HRID 1666979 reaction equation
[CH2:1]([S:4][C@:5]1([C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:33][CH:32]=2)[CH2:9][N:8]([C:10](=[O:26])[C@@H:11]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17])[C@H:7]([C:27]([O:29][CH3:30])=[O:28])[CH2:6]1)C=C.SC1N=CC=CC=1C(O)=O>ClCCl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[C:34]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:33]=[CH:32][C:31]([C@@:5]23[CH2:9][N:8]([C@H:7]([C:27]([O:29][CH3:30])=[O:28])[CH2:6]2)[C:10](=[O:26])[C@@H:11]([NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][CH2:1][S:4]3)=[CH:36][CH:35]=1

Participants

5

Reactant 2

HCID 67217834HCID 67217834, compoundHCID 178524460HCID 178524460, compound

Product 1

HCID 67444663HCID 67444663, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (2S,4R)-methyl 4-(allylthio)-4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)oct-7-enoyl)pyrrolidine-2-carboxylate (120 mg, 0.202 mmol) in Dichloromethane (50 mL) was purged with nitrogen for 30 min. And then Hoveyda-Grubbs Catalyst 2nd Generation (153 mg, 0.243 mmol) was added. The resulting green solution was heated to reflux for 5 h. The reaction was quenched with 2-Mercaptonicotinic acid (62.8 mg, 0.405 mmol) and washed with sat. Na2CO3, and brine. Dried over MgSO4, filtered, concentrated in vacuo. The brown residue was purified by Biotage column, eluted with gradient 5%˜50% EtOAc-Hexane to afford the desired product (3S,12R,14S,E)-methyl 12-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)-2-oxo-11-thia-1-azabicyclo[10.2.1]pentadec-8-ene-14-carboxylate (94 mg, 0.150 mmol, 74.0% yield) as grenish foam.

Workup

  1. temperatureThe resulting green solution was heated
  2. temperatureto reflux for 5 h
  3. washwashed with sat. Na2CO3, and brine
  4. dry with materialDried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe brown residue was purified by Biotage column
  8. washeluted with gradient 5%˜50% EtOAc-Hexane

Sources & evidence

ORD record
ord-88b4d1fa440a4a3693bb6ea2243fde9b
Source dataset
uspto-grants-2011_10
Patent number
US08044087B2

Reaction notes

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