Morpholine → HCID 53974378, compound

HRID 973923Notes

Reaction equation

HRID 973923 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([N:9]1[CH:13]([C:14]([OH:16])=O)[CH2:12][S:11][CH2:10]1)=[O:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>CN(C=O)C.C(OCC)C>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([N:9]1[CH:13]([C:14]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:16])[CH2:12][S:11][CH2:10]1)=[O:8]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 18632821HCID 18632821, compound

Product 1

HCID 53974378HCID 53974378, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

4.84 g (0.02 moles) of 3-pyroglutamyl-thiazolidine-4-carboxylic acid are suspended in 20 ml of DMF and treated with 3.25 g (0.02 mole) of carbonyldiimidazole. After no more gas is developed, 1.72 g (0.02 moles) of morpholine dissolved in 10 ml of DMF is added thereto and shaken for 1 hour. After diluting with 2 volumes of ethyl ether, the solid is filtered and water recrystallized yielding 4.35 g (70%) of product. m.p. 187°-188° C.

Workup

  1. additionis added
  2. filtrationthe solid is filtered
  3. customwater recrystallized

Sources & evidence

ORD record
ord-e284d936562446aeb7d828d6a74b97ad
Source dataset
uspto-grants-1991_11
Patent number
US05066644

Reaction notes

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