Ammonium Chloride → HCID 18931060, compound

HRID 1599027Notes

Reaction equation

HRID 1599027 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][Sn](CCCC)(CCCC)CCCC.C([Li])CCC.[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH:37][C:38]2[C:43]([O:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[O:51][CH3:52])=[C:42]([O:53][CH2:54][CH2:55][OH:56])[N:41]=[C:40](S(C)(=O)=O)[N:39]=2)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH:37][C:38]2[C:43]([O:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[O:51][CH3:52])=[C:42]([O:53][CH2:54][CH2:55][OH:56])[N:41]=[C:40]([CH2:5][O:4][CH2:3][O:2][CH3:1])[N:39]=2)(=[O:35])=[O:36])=[CH:30][CH:29]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 4193592Tributyl[(methoxymethoxy)methyl]stannaneHCID 18931061HCID 18931061, compoundHCID 178418339Butyllithium

Product 1

HCID 18931060HCID 18931060, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

##STR150## (1) To a solution of methoxymethyloxymethyltributyltin (655 mg) in tetrahydrofuran (6 ml) is added dropwise a 1.63M solution of n-butyl lithium in n-hexane (1.09 ml) at -78° C. The mixture is stirred at the same temperature for four minutes, and thereto is added a solution of 4-tert-butyl-N-[6-(2-hydroxy-ethoxy)-5-(2-methoxyphenoxy)-2-methylsulfonylpyrimidin-4-yl]benzenesulfonamide obtained in Reference Example 10-(1) (200 mg) in tetrahydrofuran (2 ml), and the mixture is stirred for 40 minutes. To the mixture is added an aqueous ammonium chloride solution, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=100:1~50:1) to give 4-tert-butyl-N-[6-(2-hydroxyethoxy)-2-methoxymethyloxymethyl-5-(2-methoxy-phenoxy)pyrimidin-4-yl]benzenesulfonamide (111 mg) as a colorless caramel.

Workup

  1. stirringthe mixture is stirred for 40 minutes
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe ethyl acetate layer is washed
  4. customdried
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=100:1~50:1)

Sources & evidence

ORD record
ord-98bd547b54bf4907bb3177c9e1fba2b3
Source dataset
uspto-grants-1998_04
Patent number
US05739333

Reaction notes

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