Morpholine → HCID 54348338, compound
Reaction equation
CS(Cl)(=O)=O.[CH3:6][O:7][C:8](=[O:20])[C@H:9]([CH2:18]O)[NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(CC)CC)C.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>ClCCl>[C:14]([O:13][C:11]([NH:10][C@@H:9]([CH2:18][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)[C:8]([O:7][CH3:6])=[O:20])=[O:12])([CH3:17])([CH3:16])[CH3:15]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methanesulphonyl chloride (0.86 mL, 11 mmol) was added dropwise to a cooled (0° C.), stirred solution of Boc-L-serine methyl ester (2.10 g, 9.6 mmol) and triethylamine (1.53 mL, 11 mmol) in dichloromethane (20 mL) under nitrogen. The mixture was stirred for 45 min, then morpholine (4.5 mL, 52 mmol) was added and the mixture stirred for a further 30 min at 0° C. followed by 1 h at room temperature. Solvent was removed in vacuo and the residue partitioned between ethyl acetate and aq. Na2CO3 solution. The layers were separated and the organic phase concentrated. The residue was azeotroped with toluene and the resulting title compound used without further purification. m/z (ES+) 289 (M+H).
Workup
- stirringthe mixture stirred for a further 30 min at 0° C.
- waitfollowed by 1 h at room temperature
- customSolvent was removed in vacuo
- customthe residue partitioned between ethyl acetate and aq. Na2CO3 solution
- customThe layers were separated
- concentrationthe organic phase concentrated
- customThe residue was azeotroped with toluene
- customthe resulting title compound used without further purification
Sources & evidence
- ORD record
- ord-d9bc63cfed3040fdb942ad04b4e1cf99
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163956B2
Reaction notes
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