4-Methylmorpholine → HCID 68710374, compound

HRID 2357031Notes

Reaction equation

HRID 2357031 reaction equation
ClC(OCC(C)C)=O.C[N:10]1[CH2:15][CH2:14]O[CH2:12][CH2:11]1.[C:16]([O:20][C:21]([NH:23][CH2:24][C:25]([C:27]1[CH:37]=[CH:36][C:30]([O:31][CH2:32][C:33]([OH:35])=O)=[CH:29][CH:28]=1)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(NCC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:16]([O:20][C:21](=[O:22])[NH:23][CH2:24][C:25]([C:27]1[CH:28]=[CH:29][C:30]([O:31][CH2:32][C:33](=[O:35])[N:10]([CH2:15][CH3:14])[CH2:11][CH3:12])=[CH:36][CH:37]=1)=[O:26])([CH3:17])([CH3:18])[CH3:19]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 8021DiethylamineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 54276808HCID 54276808, compound

Product 1

HCID 68710374HCID 68710374, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isobutyl chloroformate (0.84 ml; 6.5 mmol) was added to a stirred solution of 4-methylmorpholine (0.72 ml; 6.5 mmol) and the compound of example 1f (2.0 g; 6.5 mmol) in DMF (10 ml) at −25° C., followed by the addition of diethyl amine (0.88 ml; 8.45 mmol). The reaction mixture was stirred for 15 min., poured into a 10% aqueous NaHCO3 solution and extracted with EtOAc. The EtOAc layer was washed with brine, concentrated and crystallized using EtOAc-PE60-80° C. to obtain the title compound. Yield, 1.95 g (82%); mp, 100-01° C.; MS (EI): 364 (M+), 291, 234 (100%); analysis: C19H28N2O5 requires C, 62.62; H, 7.74; N, 7.69; found: C, 62.43; H, 7.60; N, 7.25%.

Workup

  1. extractionextracted with EtOAc
  2. washThe EtOAc layer was washed with brine
  3. concentrationconcentrated
  4. customcrystallized

Sources & evidence

ORD record
ord-be14e40716a5401b8605225e28ec9bcb
Source dataset
uspto-grants-2010_07
Patent number
US07759387B2

Reaction notes

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