Dichloromethane → HCID 87630457, compound

HRID 576257Notes

Reaction equation

HRID 576257 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=[CH:10][C:9]=2[C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][C:20]=1[CH3:29])=[O:5])[CH3:2].[C:30]1(C)[C:31]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:33]=[CH:34][CH:35]=1.Cl[CH2:42]Cl>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][O:18][S:36]([C:31]1[CH:30]=[CH:35][C:34]([CH3:42])=[CH:33][CH:32]=1)(=[O:37])=[O:38])=[CH:12][CH:11]=[CH:10][C:9]=2[C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][C:20]=1[CH3:29])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8623o-Toluenesulfonyl chlorideHCID 68936206HCID 68936206, compound

Product 1

HCID 87630457HCID 87630457, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of EXAMPLE 127B (2.0 g), toluene-2-sulfonyl chloride (1.16 g) in dichloromethane (30 mL) was added DMAP (0.305 g). The mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (300 mL) and washed with saturated aqueous sodium bicarbonate mixture, 3% aqueous HCl, water and brine. After drying over Na2SO4 and filtering, the mixture was concentrated.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate mixture, 3% aqueous HCl, water and brine
  2. dry with materialAfter drying over Na2SO4
  3. filtrationfiltering
  4. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-2af38888182241e381c94d2533809681
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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