Diethylamine → HCID 23364267, compound

HRID 1081484Notes

Reaction equation

HRID 1081484 reaction equation
[CH2:1]([O:3][C:4]1[CH:35]=[CH:34][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:31])[CH2:29]Cl)=[CH:23][C:22]=3[O:32][CH3:33])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2].C1COCC1.[CH2:41]([NH:43][CH2:44][CH3:45])[CH3:42].[C:46]([OH:53])(=[O:52])/[CH:47]=[CH:48]/[C:49]([OH:51])=[O:50]>CC(C)=O.C(OCC)C>[C:46]([OH:53])(=[O:52])/[CH:47]=[CH:48]/[C:49]([OH:51])=[O:50].[CH2:1]([O:3][C:4]1[CH:35]=[CH:34][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:31])[CH2:29][N:43]([CH2:44][CH3:45])[CH2:41][CH3:42])=[CH:23][C:22]=3[O:32][CH3:33])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 8028TetrahydrofuranHCID 444972Fumaric AcidHCID 15231549HCID 15231549, compound

Product 1

HCID 23364267HCID 23364267, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

0.55 g of the compound obtained in step A) above was mixed at 20° C. with 20 ml of THF and 10 ml of diethylamine. The reaction mixture was left to stand for 15 hours and then concentrated under vacuum. The residue was taken up with water, extracted with AcOEt and washed with 1N HCl and with water; it was dried over Na2SO4 and the solvent was evaporated off under vacuum. The residue is chromatographed on silica using DCM and then DCM/AcOEt (95/5; v/v) as the eluent to give 0.5 g of a wax, which was converted to a salt with 0.1 g of fumaric acid in 20 ml of acetone. The salt obtained is soluble in ethyl ether. m=0.2 g. M.p.=124° C.

Workup

  1. waitThe reaction mixture was left
  2. concentrationconcentrated under vacuum
  3. extractionextracted with AcOEt
  4. washwashed with 1N HCl and with water
  5. dry with materialit was dried over Na2SO4
  6. customthe solvent was evaporated off under vacuum
  7. customThe residue is chromatographed on silica
  8. customDCM/AcOEt (95/5; v/v) as the eluent to give 0.5 g of a wax, which
  9. customThe salt obtained

Sources & evidence

ORD record
ord-a4ac94422c974f09b53d8c787fcfe6ba
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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