Trifluoroacetic acid → HCID 131723653, compound

HRID 393892Notes

Reaction equation

HRID 393892 reaction equation
[NH:1]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[C@H:2]([C:11]([O:13]C(C)(C)C)=[O:12])[CH2:3][O:4][C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6].C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[NH:1]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][O:4][C:5]([O:7][CH2:8][CH:9]=[CH2:10])=[O:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131723651HCID 131723651, compound

Product 1

HCID 131723653HCID 131723653, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Morpholino-Ser(OAloc) was prepared from SER(OtBu)-OtBu. Reaction of Ser(OtBu)-OtBu with 4-morpholineacarbonyl chloride in pyridine yielded morpholino-Ser(OtBu)-OtBu. Morpholino-Ser(OtBu)-OtBu was hydrolyzed with TFA to yield morpholino-Ser. Esterification of morpholino-Ser with isobutylene in the presence of a catalytic amount of H2SO4 afforded morpholino-Ser-OtBu. Reaction of morpholino-Ser-OtBu with allyl 1-benzotriazolyl carbonate yielded morpholino-Ser(OAloc)-OtBu. Morpholino-Ser(OAloc)-OtBu was hydrolyzed with TFA in CHCl3 (1:1) to yield morpholino-Ser(OAloc).

Sources & evidence

ORD record
ord-9e9fb191b1c74ae1b286d6a7188861ce
Source dataset
uspto-grants-2004_10
Patent number
US06809176B2

Reaction notes

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