Dichloromethane → HCID 178451617, compound

HRID 713889Notes

Reaction equation

HRID 713889 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:24]([CH:28]1[CH2:33][CH2:32][CH:31](OS(C)(=O)=O)[CH2:30][CH2:29]1)([CH3:27])([CH3:26])[CH3:25].ClCCl>C(O)(C)(C)C.CC(=O)CC>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C@H:31]3[CH2:32][CH2:33][C@H:28]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:29][CH2:30]3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 10657398N-Boc-5-HydroxyindolineHCID 11128255Methanesulfonic acid 4-tert-butyl-cyclohexyl ester

Product 1

HCID 178451617HCID 178451617, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (0.6 g, 2.6 mmol) in tert-butyl alcohol (8 ml) and 2-butanone (4 mL) was added cesium carbonate (2.5 g, 7.7 mmol) followed by methanesulfonic acid 4-tert-butyl-cyclohexyl ester (1.9 g, 7.7 mmol). The mixture was heated in a sealed vial at 100° C. over night to form precipitate. The mixture was treated with dichloromethane and the precipitate was filtered off and the solvent was concentrated. The residue was purified with a silica gel column eluted with ethyl acetate in hexanes from 0 to 30% to give precipitate (0.96 g, yield: 100%). ESI-MS: 373.30 (M)+.

Workup

  1. customto form precipitate
  2. filtrationthe precipitate was filtered off
  3. concentrationthe solvent was concentrated
  4. customThe residue was purified with a silica gel column
  5. washeluted with ethyl acetate in hexanes from 0 to 30%

Sources & evidence

ORD record
ord-2c210c25e06a49b29d6831d82278e2e9
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

Loading…