4-Methylmorpholine → HCID 67419107, compound

HRID 1429356Notes

Reaction equation

HRID 1429356 reaction equation
[NH2:1][CH2:2][CH:3]([N:11]([CH2:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=O)[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])(=[O:14])=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CN1CCOCC1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C>[CH2:4]([CH:3]1[CH2:2][NH:1][C:26](=[O:28])[C:25]2[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=2[CH2:23][N:11]1[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])(=[O:14])=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 199401P,P-Diphenylphosphinic azideHCID 67418262HCID 67418262, compound

Product 1

HCID 67419107HCID 67419107, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 2f (45 mg, 0.1 mmol) in dry DMF (15 mL) was added 4-methylmorpholine (33 mg, 0.32 mmol). The mixture was stirred at rt for 10 min and DPPA (41 mg, 0.15 mmol) was added. This resulting mixture was stirred at rt for 24 h and then concentrated in vacuo to remove the solvent. The residue was dissolved in EA (10 mL), washed with saturated aqueous NH4Cl and brine, dried over anhydrous Na2SO4. Concentration in vacuo and purification by prep-TLC gave compound 2g as a white solid (40 mg, 91% yield). 1H-NMR (400 MHz, CDCl3) δ 8.03 (dd, 1H, J=8.0, 1.6 Hz), 7.47-6.99 (m, 11H), 6.86 (d, 1H, J=8.0 Hz), 6.15 (m, 1H), 5.02 (d, J=15.6 Hz, 1H), 4.22 (d, J=15.6 Hz, 1H), 4.18 (m, 1H), 3.76 (s, 3H), 3.20 (dd, J=15.2, 8.8 Hz, 1H), 3.02-2.88 (m, 2H), 2.39 (d, J=8.8 Hz, 1H). MS (ESI+) m/z: 437 [M+H]+, 459 [M+Na]+.

Workup

  1. stirringThis resulting mixture was stirred at rt for 24 h
  2. concentrationconcentrated in vacuo
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in EA (10 mL)
  5. washwashed with saturated aqueous NH4Cl and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationConcentration

Sources & evidence

ORD record
ord-f221614886404d9fb05cabf04bef617e
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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