4-Methylmorpholine → HCID 13316887, compound

HRID 2295517Notes

Reaction equation

HRID 2295517 reaction equation
[C:1]([S:9][CH2:10][CH2:11][C:12]([N:14]1[C@H:18]([C:19]([OH:21])=O)[CH2:17][S:16][C@@H:15]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.C(Cl)(=O)OCC(C)C.Cl.[CH2:45]([O:47][C:48](=[O:51])[CH2:49][NH2:50])[CH3:46]>C1COCC1.O>[CH2:45]([O:47][C:48](=[O:51])[CH2:49][NH:50][C:19]([C@@H:18]1[CH2:17][S:16][C@H:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[OH:28])[N:14]1[C:12](=[O:13])[CH2:11][CH2:10][S:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:21])[CH3:46]

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 12915689HCID 12915689, compound

Product 1

HCID 13316887HCID 13316887, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of 2.09 g of (2R,4R)-3-(S-benzoyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid dissolved in 30 ml of dry THF, 0.51 g of N-methylmorpholine is added. To the mixture 0.68 g of isobutyl chlorocarbonate is added at a temperature of -15° to -10° C. After stirring it for 15 minutes, the solution of 0.7 g of glycine ethyl ester hydrochloride and 0.51 g of N-methylmorpholine dissolved in 5 ml of THF and 15 ml of water is added to it. After stirring it for 1 hour while being back to the room temperature gradually, and then removing THF in vacuo, the mixture is extracted with ethyl acetate. The organic layer is washed with N--HCl, water, saturated aqueous sodium chloride solution, in order, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue is crystallized from ethyl acetate-benzene to give 2.43 g (82%) of the titled compound.

Workup

  1. stirringAfter stirring it for 1 hour
  2. customwhile being back to the room temperature
  3. extractionremoving THF in vacuo, the mixture is extracted with ethyl acetate
  4. washThe organic layer is washed with N
  5. dry with materialHCl, water, saturated aqueous sodium chloride solution, in order, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is crystallized from ethyl acetate-benzene

Sources & evidence

ORD record
ord-78ce7cbd252a460b970e9e89bcafd7bb
Source dataset
uspto-grants-1984_01
Patent number
US04425333

Reaction notes

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