Trifluoroacetic acid → HCID 131723649, compound

HRID 393890Notes

Reaction equation

[NH:1]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C@H:2]([C:9]([O:11]C(C)(C)C)=[O:10])[CH2:3][O:4]C(C)(C)C.C(O)(C(F)(F)F)=O>>[NH:1]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][OH:4]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 131723650HCID 131723650, compound

Product 1

HCID 131723649HCID 131723649, compound

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-25c0e6bfe0fb4c5daac6e4940a0341a4
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809176B2

Reaction notes

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