4-Methylmorpholine → Di-t-butyl [[4-[[N-[3-(1-t-butyloxycarbonylpiperidin-4-yl)propionyl]-N-methylamino]acetyl]-o-phenylene]dioxy]diacetate

HRID 234133Notes

Reaction equation

HRID 234133 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([OH:18])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:20][NH:21][CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[C:27]([O:40][CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH:26]=1)=[O:24].CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][C:16]([N:21]([CH2:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])=[C:27]([O:40][CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH:26]=2)=[O:24])[CH3:20])=[O:18])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 15125403-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acidHCID 86750213di-t-butyl [[4-[(N-methylamino)acetyl]-o-phenylene]dioxy]diacetate hydrochloride

Product 1

HCID 54497635Di-t-butyl [[4-[[N-[3-(1-t-butyloxycarbonylpiperidin-4-yl)propionyl]-N-methylamino]acetyl]-o-phenylene]dioxy]diacetateYield 44%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(1-t-butyloxycarbonylpiperidin-4-yl)propionic acid (257 mg), di-t-butyl [[4-[(N-methylamino)acetyl]-o-phenylene]dioxy]diacetate hydrochloride (446 mg), N-methylmorpholine (101 mg), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent, 442 mg), and a catalytic amount of 4-dimethylaminopyridine were dissolved in 5 ml of dimethylformamide, and the mixture was stirred at room temperature for 3 hours. After ethyl acetate (100 ml) was added to the reaction mixture, the resulting mixture was washed with water. The solvents were removed under reduced pressure. The residual mixture was purified by column chromatography on silica gel to give 285 mg of the title compound from the fraction eluted with n-hexan:ethyl acetate=3:1.

Workup

  1. washthe resulting mixture was washed with water
  2. customThe solvents were removed under reduced pressure
  3. customThe residual mixture was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9d96149cb55a44b4b5f60b3d4359b22e
Source dataset
uspto-grants-1997_01
Patent number
US05594004

Reaction notes

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