3-(Azetidin-1-yl)propan-1-ol → (1aR,5S,8S,10R,22aR)-17-[3-(azetidin-1-yl)propoxy]-5-tert-butyl-N-[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-8-carboxamide

HRID 522397Notes

Reaction equation

HRID 522397 reaction equation
[N:1]1([CH2:5][CH2:6][CH2:7][OH:8])[CH2:4][CH2:3][CH2:2]1.[C:9]([C@H:13]1[C:40](=[O:41])[N:39]2[CH2:42][C@@H:36]([CH2:37][C@H:38]2[C:43]([NH:45][C@:46]2([C:51](=[O:60])[NH:52][S:53]([C:56]3([CH3:59])[CH2:58][CH2:57]3)(=[O:55])=[O:54])[CH2:48][C@H:47]2[CH:49]=[CH2:50])=[O:44])[O:35][C:25]2=[N:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=3[C:33](O)=[C:24]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]2[CH2:61][C@H:17]2[O:16][C:15](=[O:62])[NH:14]1)([CH3:12])([CH3:11])[CH3:10]>>[N:1]1([CH2:5][CH2:6][CH2:7][O:8][C:33]2[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:26]=[C:25]3[O:35][C@H:36]4[CH2:42][N:39]([C:40](=[O:41])[C@H:13]([C:9]([CH3:11])([CH3:10])[CH3:12])[NH:14][C:15](=[O:62])[O:16][C@@H:17]5[CH2:61][C@H:18]5[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]=23)[C@H:38]([C:43]([NH:45][C@:46]2([C:51](=[O:60])[NH:52][S:53]([C:56]3([CH3:59])[CH2:57][CH2:58]3)(=[O:55])=[O:54])[CH2:48][C@H:47]2[CH:49]=[CH2:50])=[O:44])[CH2:37]4)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 204376893-(Azetidin-1-yl)propan-1-olHCID 178455699HCID 178455699, compound

Product 1

HCID 117598934(1aR,5S,8S,10R,22aR)-17-[3-(azetidin-1-yl)propoxy]-5-tert-butyl-N-[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-8-carboxamide

Procedure

The title compound was prepared using the same method as described in Example 75, using the 3-(azetidin-1-yl)propan-1-ol and (1aR,5S,8S,10R,22aR)-5-tert-butyl-N-[(1R,2S)-2-ethenyl-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-17-hydroxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-8-carboxamide (Example 120). LRMS (ES+) m/z 863.50 (M+H)+.

Sources & evidence

ORD record
ord-e555143514724182b520726e3f3b105d
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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