Methanol → HCID 86635944, compound

HRID 561885Notes

Reaction equation

HRID 561885 reaction equation
[CH2:1]1COCC1.CO.[CH:8]1([N:11]([CH2:44][C:45]2[CH:50]=[C:49]([O:51][CH2:52][CH2:53][CH2:54]SC)[N:48]=[C:47]([CH2:57][CH2:58][CH2:59][O:60][CH3:61])[CH:46]=2)[C:12](=[O:43])[CH:13]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][C:34]3[C:39]([Cl:40])=[CH:38][C:37]([CH3:41])=[CH:36][C:35]=3[Cl:42])=[CH:26][CH:25]=2)[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:10][CH2:9]1.O[O:63][S:64]([O-:66])=O.[K+]>O>[CH:8]1([N:11]([CH2:44][C:45]2[CH:50]=[C:49]([O:51][CH2:52][CH2:53][CH2:54][S:64]([CH3:1])(=[O:66])=[O:63])[N:48]=[C:47]([CH2:57][CH2:58][CH2:59][O:60][CH3:61])[CH:46]=2)[C:12](=[O:43])[CH:13]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][C:34]3[C:39]([Cl:40])=[CH:38][C:37]([CH3:41])=[CH:36][C:35]=3[Cl:42])=[CH:26][CH:25]=2)[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 86635945HCID 86635945, compound

Product 1

HCID 86635944HCID 86635944, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 2:1:1 (v/v/v) THF:MeOH:water solution (0.1 M) of tert-butyl (3-[cyclopropyl({2-(3-methoxypropyl)-6-[3-(methylthio)propoxy]pyridin-4-yl]methyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate from Example 100, Step 1 (1 eq.) was added Oxone™ (2.2 eq.) The resulting solution was stirred at RT for 2 h. The reaction was quenched with sat. aq. NaHCO3 and then extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 95:5 (v/v) CH2Cl2:EtOH) afforded the title compound as a colorless oil.

Workup

  1. customThe reaction was quenched with sat. aq. NaHCO3
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 95:5 (v/v) CH2Cl2:EtOH)

Sources & evidence

ORD record
ord-f222e81d128b4278a0de0aa16db4c67e
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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