HCID 131723652, compound → HCID 131723651, compound

HRID 393888Notes

Reaction equation

HRID 393888 reaction equation
[NH:1]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C@H:2]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:3][OH:4].[C:18](=O)([O:23]C1C2N=NNC=2C=CC=1)[O:19][CH2:20][CH:21]=[CH2:22]>>[NH:1]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C@H:2]([C:5]([O:7][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:6])[CH2:3][O:4][C:18]([O:19][CH2:20][CH:21]=[CH2:22])=[O:23]

Participants

3

Reactant 2

HCID 131723652HCID 131723652, compoundHCID 178459894HCID 178459894, compound

Product 1

HCID 131723651HCID 131723651, compound

Procedure

Morpholino-Ser(OAloc) was prepared from Ser(OtBu)-OtBu. Reaction of Ser(OtBu)-OtBu with 4-morpholinecarbonyl 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-de523b597c4e46b6bbef9b36fb995823
Source dataset
uspto-grants-2004_10
Patent number
US06809176B2

Reaction notes

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