4-Methylmorpholine → Ethyl acetate ethanol ammonia

HRID 322498Notes

Reaction equation

HRID 322498 reaction equation
[O:1]=[C:2]1[CH:7](CCC2C=CC3CCCNC=3N=2)CCC[N:3]1[CH2:20][C:21]([OH:23])=[O:22].CN1CCO[CH2:27][CH2:26]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CC#N>[NH3:3].[CH3:7][CH2:2][OH:1].[CH3:26][CH2:27][O:23][C:21]([CH3:20])=[O:22]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22008800HCID 22008800, compound

Product 1

HCID 86587043Ethyl acetate ethanol ammonia

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 1-8 (71 mg, 0.20 mmol), 1-9 (59 mg, 0.22 mmol) (Rico et al., J. Org. Chem., 1993, 58, 7948), NMM (88 μL, 0.8 mmol), and CH3CN (25 mL) was treated with BOP (97 mg, 0.22 mmol). After 24 h, the reaction mixture was concentrated to dryness, dissolved in EtOAc, and then washed with H2O, dried (MgSO4), and concentrated. Flash chromatography (silica, 10% (NH3/EtOH/EtOAc) gave 1-10 as a colorless gum.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. dissolutiondissolved in EtOAc
  3. washwashed with H2O
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6ed823079f2249778c51d799d559c2c1
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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