Phthalimide → (25R)-16-oxo-26-phthalimidocholesterol

HRID 327770Notes

Reaction equation

[O:1]=[C:2]1[CH2:27][C@@H:26]2[C@:13]([CH3:30])([CH2:14][CH2:15][C@H:16]3[C@H:25]2[CH2:24][CH:23]=[C:22]2[C@:17]3([CH3:29])[CH2:18][CH2:19][C@H:20]([OH:28])[CH2:21]2)[C@H:3]1[C@H:4]([CH3:12])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:11])[CH2:9]O.[C:31]1(=[O:41])[NH:35][C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]12>>[O:1]=[C:2]1[CH2:27][C@@H:26]2[C@:13]([CH3:30])([CH2:14][CH2:15][C@H:16]3[C@H:25]2[CH2:24][CH:23]=[C:22]2[C@:17]3([CH3:29])[CH2:18][CH2:19][C@H:20]([OH:28])[CH2:21]2)[C@H:3]1[C@H:4]([CH3:12])[CH2:5][CH2:6][CH2:7][C@@H:8]([CH3:9])[CH2:11][N:35]1[C:31](=[O:41])[C:32]2=[CH:40][CH:39]=[CH:38][CH:37]=[C:33]2[C:34]1=[O:36]

Participants

Reactant 2

HCID 6809Phthalimide

HCID 13873472(25R)-16-oxo-26-hydroxycholesterol2×

Product 1

HCID 9832896(25R)-16-oxo-26-phthalimidocholesterol

Procedure

Thereafter, (25R)-16-oxo-26-hydroxycholesterol (9) is converted to (25R)-16-oxo-26-hydroxycholesterol-26-tosylate (8) directly or indirectly by solvolysis of a (25R)-16-oxo-26-hydroxycholesterol-3β,26--ditosylate (7). Intermediate (8) is then subjected to displacement reaction with a phthalimide salt to form (25R)-16-oxo-26-phthalimidocholesterol (5). The reaction conditions and reagents for effecting all these conversions are the same as described above.

Sources & evidence

ORD record: ord-6817099fc27f4fc8bfcd015557816d11
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05274088

Reaction notes

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