Methanol → tert-Butyl (3-{cyclopropyl {3-(3-methoxypropyl)-5-[3-(methylsulfonyl)propoxy]benzyl}amino)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

HRID 561875Notes

Reaction equation

HRID 561875 reaction equation
[CH:1]1([N:4]([CH2:37][C:38]2[CH:43]=[C:42]([O:44][CH2:45][CH2:46][CH2:47]SC)[CH:41]=[C:40]([CH2:50][CH2:51][CH2:52][O:53][CH3:54])[CH:39]=2)[C:5](=[O:36])[CH:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][O:26][C:27]3[C:32]([Cl:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=3[Cl:35])=[CH:19][CH:18]=2)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.CO.O[O:58][S:59]([O-:61])=O.[K+].[C:63](=O)(O)[O-].[Na+]>O>[CH:1]1([N:4]([CH2:37][C:38]2[CH:43]=[C:42]([O:44][CH2:45][CH2:46][CH2:47][S:59]([CH3:63])(=[O:61])=[O:58])[CH:41]=[C:40]([CH2:50][CH2:51][CH2:52][O:53][CH3:54])[CH:39]=2)[C:5](=[O:36])[CH:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][O:26][C:27]3[C:32]([Cl:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=3[Cl:35])=[CH:19][CH:18]=2)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 86635936tert-Butyl (3-{cyclopropyl {3-(3-methoxypropyl)-5-[3-(methylthio)propoxy]benzyl}amino)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

Product 1

HCID 86635937tert-Butyl (3-{cyclopropyl {3-(3-methoxypropyl)-5-[3-(methylsulfonyl)propoxy]benzyl}amino)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To tert-butyl (3-{cyclopropyl{3-(3-methoxypropyl)-5-[3-(methylthio)propoxy]benzyl}amino)-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate from Example 75, Step 2 (1 eq.) in a 1:1 (v/v) methanol:water solution (0.05 M) was added Oxone™ (2.5 eq.) and sodium bicarbonate (10 eq.). The reaction mixture was stirred at RT for 1 h. The volatiles were then removed in vacuo and the result residue was extracted with ether. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 3:2 (v/v) Hex:EtOAc→1:3 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customThe volatiles were then removed in vacuo
  2. extractionthe result residue was extracted with ether
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 3:2 (v/v) Hex:EtOAc→1:3 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-15006130bcd646aaa379e1733046b830
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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