Potassium Bicarbonate → HCID 58875096, compound

HRID 2355252Notes

Reaction equation

HRID 2355252 reaction equation
C(=O)([O-])O.[K+].Br[CH2:7][C:8]1[O:9][C:10](=[O:14])[O:11][C:12]=1[CH3:13].[C:15]1([S:21]([NH:24][C:25]2[CH:26]=[C:27]([C@@H:31]([OH:51])[CH2:32][NH:33][C:34]([CH3:50])([CH3:49])[CH2:35][CH2:36][N:37]3[C:45]4[C:40](=[CH:41][C:42]([C:46]([OH:48])=[O:47])=[CH:43][CH:44]=4)[CH:39]=[CH:38]3)[CH:28]=[CH:29][CH:30]=2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[C:15]1([S:21]([NH:24][C:25]2[CH:26]=[C:27]([C@@H:31]([OH:51])[CH2:32][NH:33][C:34]([CH3:49])([CH3:50])[CH2:35][CH2:36][N:37]3[C:45]4[C:40](=[CH:41][C:42]([C:46]([O:48][CH2:7][C:8]5[O:9][C:10](=[O:14])[O:11][C:12]=5[CH3:13])=[O:47])=[CH:43][CH:44]=4)[CH:39]=[CH:38]3)[CH:28]=[CH:29][CH:30]=2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-oneHCID 16660493HCID 16660493, compound

Product 1

HCID 58875096HCID 58875096, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium hydrogen carbonate (331 mg, 3.30 mmol) and 4-bromomethyl-5-methyl-[1,3]dioxol-2-one (Chem. Pharm. Bull. 1984, vol. 32 (6), page 2241-2248) (505 mg, 2.36 mmol) are added to a solution of 1-{3-[(R)-2-[3-(phenylsulphonylamino)-phenyl]-2-hydroxy-ethylamino]-3-methyl-butyl}-1H-indole-5-carboxylic acid-hydrotrifluoroacetate (Example 6; 1.0 g, 1.57 mmol) in 10 ml DMF. Then the reaction mixture is stirred for 18 hours at RT. Then the solid is filtered off and the filtrate is freed from the solvent in vacuo. The residue is chromatographed on silica gel (DCM/methanol/ammonia=100:0:0→90:10:0.1).

Workup

  1. filtrationThen the solid is filtered off
  2. customThe residue is chromatographed on silica gel (DCM/methanol/ammonia=100:0:0→90:10:0.1)

Sources & evidence

ORD record
ord-b4a471a08d714f75b59e5e2d95404698
Source dataset
uspto-grants-2010_07
Patent number
US07754756B2

Reaction notes

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