Water → HCID 59494554, compound

HRID 872011Notes

Reaction equation

HRID 872011 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[CH:9]1([N:12]([CH2:28][C:29]2[CH:34]=[C:33]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:32]=[C:31]([OH:41])[CH:30]=2)[C:13]([C@@H:15]2[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]2)=[O:14])[CH2:11][CH2:10]1.O>CN(C)C=O>[CH:9]1([N:12]([CH2:28][C:29]2[CH:34]=[C:33]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:32]=[C:31]([O:41][CH3:1])[CH:30]=2)[C:13]([C@@H:15]2[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]2)=[O:14])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59494840HCID 59494840, compound

Product 1

HCID 59494554HCID 59494554, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (54 mg) and methyl iodide (24 μL) were added to a solution of tert-butyl(2R)-2-({cyclopropyl[3-hydroxy-5-(3-methoxypropoxy)benzyl]amino}carbonyl)morpholin-4-carboxylate (a compound obtained in Reference Example 12, 120 mg) in N,N-dimethylformamide (6 ml) and the mixture was stirred at room temperature for 2 hours. Water was added to the mixture under ice-cooling and it was extracted with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over sodium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1) to give tert-butyl(2R)-2-({cyclopropyl[3-methoxy-5-(3-methoxypropoxy)benzyl]amino}carbonyl)morpholin-4-carboxylate (88 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. extractionit was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine successively
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-212c7f27f012481cb04f99025fb21a0b
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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