4-Methylmorpholine → HCID 54216343, compound

HRID 636979Notes

Reaction equation

HRID 636979 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.[CH2:11]([O:13][C:14]([NH:16][C@@H:17]([C:21]([S:24][CH:25]([CH3:27])[CH3:26])([CH3:23])[CH3:22])[C:18](O)=[O:19])=[O:15])[CH3:12].CN1CCOCC1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH3:2][O:3][C:4]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:18](=[O:19])[C@@H:17]([NH:16][C:14]([O:13][CH2:11][CH3:12])=[O:15])[C:21]([S:24][CH:25]([CH3:27])[CH3:26])([CH3:22])[CH3:23])=[O:10]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 2733200methyl L-prolinate hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 54283045HCID 54283045, compound

Product 1

HCID 54216343HCID 54216343, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (L)-proline methyl ester hydrochloride (0.28 g), 2-(R)-ethoxycarbonylamino-3-isopropylsulfanyl-3-methyl-butyric acid (0.44 g), N-methyl morpholine (0.73 mL) and 0.54 g of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) in 10 mL of dry N,N-dimethylformamide was stirred for 16 h at ambient temperature. The volatiles were pumped off and water was added followed by extraction with ethyl acetate and concentration of the organic layer. The remaining residue was purified by silica chromatography (ethyl acetate/isohexane=1/1) to give 0.45 g (72%) of the title compound as a colorless oil. (+)-APCI-MS: 375 (MH+).

Workup

  1. extractionfollowed by extraction with ethyl acetate and concentration of the organic layer
  2. customThe remaining residue was purified by silica chromatography (ethyl acetate/isohexane=1/1)

Sources & evidence

ORD record
ord-44b5137e48f94801b44bdd34680456a1
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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