4-Morpholinecarbonyl chloride → HCID 131723646, compound

HRID 852809Notes

Reaction equation

HRID 852809 reaction equation
[NH2:1][C@H:2]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N:19]1(C(Cl)=O)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>N1C=CC=CC=1>[NH:1]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[C@H:2]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 848104-Morpholinecarbonyl chlorideHCID 22858196HCID 22858196, compound

Product 1

HCID 131723646HCID 131723646, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Morpholino-Ser(OBn) was prepared from N-Fmoc-Ser(OBn). Esterification of N-Fmoc-Ser(OBn) with isobutylene in the presence of a catalytic amount of H2SO4 afforded N-Fmoc-Ser(OBn)-OtBu. The Fmoc group was removed with piperidine in CH2Cl2 to produce Ser(OBn)-OtBu. Reaction of Ser(OBn)-OtBu with 4-morpholinecarbonyl chloride in pyridine yielded morpholino-Ser(OBn)-OtBu. Morpholino-Ser(OBn)-OtBu was hydrolyzed with TFA in CH2Cl2 to yield morpholine-Ser(OBn).

Sources & evidence

ORD record
ord-6d9e4f42d7a9451a9b69a401b133248d
Source dataset
uspto-grants-2007_08
Patent number
US07253207B2

Reaction notes

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