4-Methylmorpholine → HCID 13316875, compound

HRID 2295518Notes

Reaction equation

HRID 2295518 reaction equation
[C:1]([S:4][CH2:5][CH2:6][C:7]([N:9]1[C@H:13]([C:14]([OH:16])=O)[CH2:12][S:11][C@@H:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=[O:8])(=[O:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)OCC(C)C.Cl.[CH2:40]([O:42][C:43](=[O:46])[CH2:44][NH2:45])[CH3:41]>C1COCC1>[CH2:40]([O:42][C:43](=[O:46])[CH2:44][NH:45][C:14]([C@@H:13]1[CH2:12][S:11][C@H:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])[N:9]1[C:7](=[O:8])[CH2:6][CH2:5][S:4][C:1](=[O:3])[CH3:2])=[O:16])[CH3:41]

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 13316857HCID 13316857, compound

Product 1

HCID 13316875HCID 13316875, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The suspension is prepared by using 1.78 g of (2R,4R)-3-(S-acetyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid, 0.51 g of N-methylmorpholine and 0.68 g of isobutyl chlorocarbonate. To the suspension the solution of 0.7 g of glycine ethyl ester hydrochloride and 0.51 g of N-methylmorpholine dissolved in aqueous THF is added, and treated in the same manner as Example 10 to give 1.8 g (82%) of the titled compound.

Workup

  1. customThe suspension is prepared
  2. additionis added
  3. additiontreated in the same manner as Example 10

Sources & evidence

ORD record
ord-3d35f0e2784c4896b28105c4b3c7609c
Source dataset
uspto-grants-1984_01
Patent number
US04425333

Reaction notes

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