Myristic Acid → (E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-non-6-enoic acid [(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-amide

HRID 2224029Notes

Reaction equation

HRID 2224029 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C@H:11]1[CH2:17][N:16]([CH3:18])[C:15](=[O:19])[C@@H:14]([NH:20][C:21](=[O:40])[C@@H:22]([C@H:25]2[C@H:30]([OH:31])[C@@H:29](/[CH:32]=[CH:33]/[C:34]([CH3:37])([CH3:36])[CH3:35])[O:28]C(C)(C)[O:26]2)[O:23][CH3:24])[CH2:13][CH2:12]1)=[N+:2]=[N-:3].C(O)(=O)CCCCCCCCCCCCC>>[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C@H:11]1[CH2:17][N:16]([CH3:18])[C:15](=[O:19])[C@@H:14]([NH:20][C:21](=[O:40])[C@H:22]([O:23][CH3:24])[C@H:25]([OH:26])[C@@H:30]([OH:31])[C@H:29]([OH:28])/[CH:32]=[CH:33]/[C:34]([CH3:35])([CH3:37])[CH3:36])[CH2:13][CH2:12]1)=[N+:2]=[N-:3]

Participants

3

Reactant 2

HCID 11005Myristic AcidHCID 86609580(R)-N-[(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-2-[(4R,5R,6R)-6-((E)-3,3-dimethyl-but-1-enyl)-5-hydroxy-2,2-dimethyl-[1,3]dioxan-4-yl]-2-methoxy-acetamide

Product 1

HCID 59840149(E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethyl-non-6-enoic acid [(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-amide

Procedure

Following the procedure of Example 1 m) except (R)-N-[(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-2-[(4R,5R,6R)-6-((E)3,3-dimethyl-but-1-enyl)-5-hydroxy-2,2-dimethyl-[1,3]dioxan-4-yl]-2-methoxy-acetamide is substituted for tetradecanoic acid (3R,6S-6-{(R)-2-[(4R,5R,6R)-6-((E)-3,3-dimethyl-but-1-enyl)-5-hydroxy-2,2-dimethyl-[1,3]dioxan-4-yl]-2-methoxy-acetylamino}-7-oxo-1-pyridin-3-ylmethyl-azepan-3-yl ester. MS (ESI) 528.0 (M+H)+

Sources & evidence

ORD record
ord-2fd56b37d46640efa7c3405b0464ee6e
Source dataset
uspto-grants-2008_05
Patent number
US07378410B2

Reaction notes

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