2-Morpholinoethanol → HCID 72192066, compound

HRID 1487050Notes

Reaction equation

HRID 1487050 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1)(=[O:12])=[O:11].[O:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31]O)[CH2:26][CH2:25]1.FC(F)(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)CCC1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CN(C=O)C.O.CO.O.CN(C=O)C.O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:31][CH2:30][N:27]2[CH2:28][CH2:29][O:24][CH2:25][CH2:26]2)[CH:14]=1)(=[O:11])=[O:12]

Participants

9

Reactant 4

HCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11422653[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluorodecyl)phenyl] diphenylphosphineHCID 86731581HCID 86731581, compound

Product 1

HCID 72192066HCID 72192066, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 21962138N,N-Dimethylformamide--water (1/1)SolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
20 °C

Procedure

N-(2,4-dimethylphenyl)-3-hydroxy-N-isobutylbenzenesulfonamide (76.9 mg, 0.231 mmol), 2-morpholinoethanol (0.035 mL, 0.288 mmol) and (4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl)diphenylphosphine (204 mg, 0.288 mmol) were added to a vessel. Tetrahydrofuran (THF) (4 mL) was added followed by diisopropyl diazene-1,2-dicarboxylate (DIAD) (0.056 ml, 58.3 mg 0.288 mmol). The reaction vial was sealed and left to stir overnight at 20° C. The reaction mixture was concentrated in vacuo and then diluted with ethyl acetate (25 mL) and water (25 mL). The organic fraction was separated, dried and concentrated in vacuo to give the crude product. The crude product was dissolved in DMF:H2O (9:1) (1 mL) and loaded onto a fluorous column (pre-conditioned with 1 mL DMF, followed by 6 mL MeOH:H2O (5:1)). The semi-purified material was eluted with 6 mL MeOH:H2O (5:1). This was concentrated and dissolved in 1:1 MeOH:DMSO (1 mL) then further purified by mass directed autoprep (formic acid modifier). The relevant fractions were concentrated under a stream of nitrogen to give the required product, 17 mg. LCMS [LCMS1] Rt 1.03 min, m/z (ES+) 447 (M+H).

Workup

  1. customThe reaction
  2. customvial was sealed
  3. waitleft
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. additiondiluted with ethyl acetate (25 mL) and water (25 mL)
  6. customThe organic fraction was separated
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customto give the crude product
  10. washThe semi-purified material was eluted with 6 mL MeOH:H2O (5:1)
  11. concentrationThis was concentrated
  12. dissolutiondissolved in 1:1 MeOH
  13. customDMSO (1 mL) then further purified by mass
  14. concentrationThe relevant fractions were concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-620618eb40534e4eaa296f7d39f5b4d3
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

Loading…