Sodium Chloride → HCID 10408263, compound

HRID 359761Notes

Reaction equation

HRID 359761 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:15][CH:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH:17]([OH:21])[C:18](O)=[O:19].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.CN1CCOCC1.[Cl-].[Na+]>CN(C)C=O>[OH:21][C@H:17]1[C:18](=[O:19])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][C:3]=2[S:15][C@H:16]1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 79724-MethylmorpholineHCID 199401P,P-Diphenylphosphinic azideHCID 15687402HCID 15687402, compound

Product 1

HCID 10408263HCID 10408263, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.2 g of 3-(2-amino-5-phenoxyphenyl)thio-2-hydroxy-3-(4-methoxyphenyl)propionic acid [prepared as described in step (b) above] were dissolved in 11 ml of dimethylformamide, and 1.38 ml of diphenylphosphorylazide was added, whilst ice-cooling, the mixture was then stirred for 30 minutes. At the end to this time, 1.38 ml of N-methylmorpholine was added to the mixture, which was then stirred at the same temperature for 30 minutes, and then at room temperature for 2 hours. After this, an aqueous solution of sodium chloride was added and the mixture was extracted twice with ethyl acetate. The extracts were combined, washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was triturated in diethyl ether, filtered and washed with diethyl ether, to give 1.13 g of the title compound.

Workup

  1. temperaturecooling
  2. stirringwas then stirred at the same temperature for 30 minutes
  3. waitat room temperature for 2 hours
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. washwashed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe residue was triturated in diethyl ether
  9. filtrationfiltered
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-1a7011ac73d24a24b4e76c69ad8b4651
Source dataset
uspto-grants-1991_03
Patent number
US05002942

Reaction notes

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