4-Methylmorpholine → Ammonium Hydroxide

HRID 617904Notes

Reaction equation

HRID 617904 reaction equation
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][NH:14][C:15]([CH2:17][C:18]([OH:20])=O)=[O:16].F[P-](F)(F)(F)(F)F.[N:28]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36]C=2N=N1.[CH3:48][N:49]1CCOCC1.[C:55]([O:58][CH2:59][CH3:60])(=[O:57])[CH3:56]>CN(C=O)C>[NH4+:1].[OH-:16].[N:49]1[CH:36]=[CH:35][CH:34]=[C:33]([C@@H:32]([NH:28][C:18](=[O:20])[CH2:17][C:15](=[O:16])[NH:14][CH2:13][CH2:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[CH2:6][CH2:7][CH2:8][NH:9][C:10]=3[N:1]=2)[CH2:56][C:55]([O:58][CH2:59][CH3:60])=[O:57])[CH:48]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 21850001HCID 21850001, compound

Product 2

HCID 14923Ammonium HydroxideHCID 53704821HCID 53704821, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-10 (0.072 g, 0.24 mmol), 1-11 (0.064 g, 0.24 mmol), BOP (0.16 g, 0.36 mmol), and NMM (0.13 mL, 1.2 mmol) in DMF (2 mL) was stirred at ambient temperature for 20 h. The mixture was diluted with ethyl acetate, washed with water, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed on silica gel, eluting with 1:3 [20:1:1 ethanol:NH4OH:H2O/EtOAc to give 1-12 as a colorless glass.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. customremoval of the solvent
  4. customthe residue was chromatographed on silica gel
  5. washeluting with 1:3 [20:1:1 ethanol

Sources & evidence

ORD record
ord-08a72ce4b27148da87925584ad3eda00
Source dataset
uspto-grants-1999_09
Patent number
US05952341

Reaction notes

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