4-Methylmorpholine → HCID 10408263, compound

HRID 359769Notes

Reaction equation

HRID 359769 reaction equation
CN1CCOCC1.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][C:10]=1[S:22][C@@H:23]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C@@H:24]([OH:28])[C:25](O)=[O:26].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C.O>[OH:28][C@H:24]1[C:25](=[O:26])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][C:10]=2[S:22][C@H:23]1[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1

Participants

7

Reactant 3

HCID 79724-MethylmorpholineHCID 199401P,P-Diphenylphosphinic azideHCID 10093047HCID 10093047, compound

Product 1

HCID 10408263HCID 10408263, compoundYield 54.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

1,5 ml of N-methylmorpholine was added, whilst ice-cooling, to a solution of 1.74 g of (2S, 3S)-3-(2- amino-5-phenoxyphenyl)thio-2-hydroxy-3-(4-methoxyphenyl)propionic acid [prepared as described in step (b) above] and 1,5 g of diphenylphosphorylaZide dissolved in 19 ml of dimethylformamide, and the mixture was stirred at room temperature for 16 hours. At the end of this time, ethyl acetate and water were added to the reaction mixture, and the resulting mixture was shaken to mix it thoroughly The ethyl acetate layer was then separated and dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation under reduced pressure. The crystalline residue was collected by filtration using diethyl ether and diisopropyl ether to afford 0.90 g of the title compound melting at 181-183° C.

Workup

  1. stirringthe resulting mixture was shaken
  2. customwas then separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed by evaporation under reduced pressure
  5. filtrationThe crystalline residue was collected by filtration

Sources & evidence

ORD record
ord-09ad636c9c214e5f9cf548f3682c1c72
Source dataset
uspto-grants-1991_03
Patent number
US05002942

Reaction notes

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