4-Methylmorpholine → HCID 14881553, compound

HRID 704422Notes

Reaction equation

HRID 704422 reaction equation
[CH:1]([N:3]1[CH:7]([C:8]([OH:10])=O)[CH2:6][S:5][CH:4]1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:2].Cl.[CH3:18][O:19][C:20](=[O:27])[C@H:21]([CH2:23][CH2:24][S:25][CH3:26])[NH2:22].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.CN(C)C=O>[CH3:18][O:19][C:20](=[O:27])[C@H:21]([CH2:23][CH2:24][S:25][CH3:26])[NH:22][C:8]([CH:7]1[CH2:6][S:5][CH:4]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:3]1[CH:1]=[O:2])=[O:10]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10922588HCID 10922588, compoundHCID 11435579L-Methionine, methyl ester, hydrochloride

Product 1

HCID 14881553HCID 14881553, compoundYield 39,190.199%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.3 g of N-formyl-2-(3-pyridyl)thiazolidine-4-carboxylic acid in 50 ml of tetrahydrofuran plus 10 ml of N,N-dimethylformamide, there were added, at 4° C. or below, 1.16 g of L-methionine methyl ester hydrochloride, 1.17 g of 1-hydroxybenzotriazole, 560 mg of N-methylmorpholine and 1.32 g of dicyclohexylcarbodiimide, in that order. The mixture was stirred at 4° C. or below for 1 hour and then at room temperature for 1 hour. The reaction mixture was then treated in the same manner as in Example 1. Purification by silica gel column chromatography [eluent: chloroform-methanol (9:1)] gave 820 g of [N-formyl-2-(3-pyridyl)thiazolidine-4-carbonyl]-L-methionine methyl ester as an oil.

Workup

  1. waitat room temperature for 1 hour
  2. additionThe reaction mixture was then treated in the same manner as in Example 1
  3. customPurification by silica gel column chromatography [eluent: chloroform-methanol (9:1)]

Sources & evidence

ORD record
ord-fcb31ae5aba74dd1bf01392d8a9c86f8
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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