4-Methylmorpholine → HCID 86751081, compound

HRID 265862Notes

Reaction equation

HRID 265862 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=O)=[O:7].[C:17]([N:27]1[CH2:32][CH2:31][CH:30]([CH2:33][NH2:34])[CH2:29][CH2:28]1)([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.C(Cl)(Cl)Cl>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:9]=[C:10]([C:11]([NH:34][CH2:33][CH:30]2[CH2:31][CH2:32][N:27]([C:17]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[CH2:28][CH2:29]2)=[O:13])[CH:14]=[CH:15][CH:16]=1)=[O:7]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 19034109HCID 19034109, compoundHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Product 1

HCID 86751081HCID 86751081, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 8-2 (0.44 g, 2 mmoles) in DMF (25 ml) was treated with N-(CBZ-4-piperidinyl)methyl amine (0.53 g, 2 mmoles) (8-3), HOBT (0.3 g, 2.2 mmoles) EDC (0.44 g, 2.3 mmoles) followed by NMM (0.4 g, 4 mmoles) and the resulting solution was stirred for 16 hours. The solvent was removed and the residue was taken up in H2O and extracted with EtOAc. The organic extract was washed with 10% KHSO4 solution, brine, saturated NaHCO3 solution, brine and dried (Na2SO4). Solvent removal gave a residue that was purified by flash chromatography on silica gel eluting with CHCl3 (97)/MeOH(3) to give pure 8-4. Rf 0.35 (silica, CHCl3 (95)/MeOH(5). ##STR55##

Workup

  1. customThe solvent was removed
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with 10% KHSO4 solution, brine, saturated NaHCO3 solution, brine
  5. dry with materialdried (Na2SO4)
  6. customSolvent removal
  7. customgave a residue that
  8. customwas purified by flash chromatography on silica gel eluting with CHCl3 (97)/MeOH(3)
  9. customto give pure 8-4

Sources & evidence

ORD record
ord-c7e0244695b7497e8af9307a3d343ed2
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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