Ammonium Chloride → HCID 21138131, compound

HRID 1358886Notes

Reaction equation

HRID 1358886 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][C@@H:15]3[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][S:32]([CH2:35][CH2:36][CH2:37][C:38]([F:44])([F:43])[C:39]([F:42])([F:41])[F:40])(=[O:34])=[O:33])=[CH:22][CH:21]=3)([CH3:13])[C:11](=O)[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[CH3:46][O-].[Na+].[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH2:46]=[C:11]1[CH2:10][CH2:9][C@H:8]2[C@H:7]3[C@H:16]([C@@H:15]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][S:32]([CH2:35][CH2:36][CH2:37][C:38]([F:43])([F:44])[C:39]([F:40])([F:42])[F:41])(=[O:33])=[O:34])=[CH:22][CH:21]=4)[CH2:14][C@:12]12[CH3:13])[C:17]1[CH:18]=[CH:19][C:2]([OH:1])=[CH:3][C:4]=1[CH2:5][CH2:6]3

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 21138145HCID 21138145, compound

Product 1

HCID 21138131HCID 21138131, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 312751,4-DioxaneSolvent

Procedure

500 mg of the product obtained in Example 73 is added to a mixture containing 815 mg of methyltriphenylphosphonium bromide, 5 cm3 of dioxan and 125 mg of sodium methylate. Agitation is carried out for 16 hours at ambient temperature, 100 cm3 of an aqueous solution of ammonium chloride is added, followed by extracting with methylene chloride, drying, eliminating the solvent under reduced pressure and chromatographing the residue on silica (eluant: cyclohexane-ethyl acetate 7-3). 80 mg of expected product is obtained.

Workup

  1. extractionby extracting with methylene chloride
  2. customdrying

Sources & evidence

ORD record
ord-477cc8bae5f14d778bd842fb5a5b03f4
Source dataset
uspto-grants-2003_07
Patent number
US06596885B2

Reaction notes

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