Water → HCID 86688735, compound

HRID 1752636Notes

Reaction equation

HRID 1752636 reaction equation
C(N(C(C)C)CC)(C)C.[OH:10][CH2:11][CH2:12][O:13][C:14](=[O:38])[CH2:15][C:16]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[N:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:17]=1[CH3:37].[CH3:39][S:40](Cl)(=[O:42])=[O:41].O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:39][S:40]([O:10][CH2:11][CH2:12][O:13][C:14](=[O:38])[CH2:15][C:16]1[CH:20]=[C:19]([C:21]2[CH:22]=[CH:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=2)[N:18]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:17]=1[CH3:37])(=[O:42])=[O:41]

Participants

7

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 56833736HCID 56833736, compound

Product 1

HCID 86688735HCID 86688735, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

DMAP (0.03 mmol) and diisopropylethylamine (DPEA) (0.5 mmol) are added to a solution of 2-hydroxyethyl-2-[1-phenyl-2-methyl-5-(4-methylsulphonylphenyl)-1H-pyrrol-3-yl)acetate in DCM (10 ml), at 0° C., MsCl (0.6 mmol) is added and it is stirred for 3 h, at RT. Then H2O is added (5 ml) and it is stirred for 1 h, the phases are separated and the organic phase is washed with NaHCO3 and then with H2O. It is dried and concentrated. The raw product is purified by chromatography (silica; hexane/EtOAc). Oil, yield 76%. 1H NMR 200 MHz (CDCl3) δ (ppm): 2.05 (s, 3H), 2.96 (s, 6H), 3.50 (s, 2H), 4.13-4.33 (m, 4H), 6.51 (s, 1H), 7.08-7.14 (m, 4H), 7.37-7.41 (m, 3H), 7.62 (d, 2H, J=8.6). MS-ESI: m/z 515 (M+Na+).

Workup

  1. stirringis stirred for 1 h
  2. customthe phases are separated
  3. washthe organic phase is washed with NaHCO3
  4. customIt is dried
  5. concentrationconcentrated
  6. customThe raw product is purified by chromatography (silica; hexane/EtOAc)

Sources & evidence

ORD record
ord-03fd160225774730999fc98a0abc99fa
Source dataset
uspto-grants-2015_10
Patent number
US09162979B2

Reaction notes

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