Trifluoroacetic acid → HCID 131723647, compound

HRID 852810Notes

Reaction equation

HRID 852810 reaction equation
[NH:1]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[C@H:2]([C:12]([O:14]C(C)(C)C)=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[NH2:1][C@H:2]([C:12]([OH:14])=[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 6422Trifluoroacetic acidHCID 131723646HCID 131723646, compound

Product 1

HCID 131723647HCID 131723647, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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-f5db3ccc1cac4f1ea4dae1a72b9f7543
Source dataset
uspto-grants-2007_08
Patent number
US07253207B2

Reaction notes

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