4-(2-Bromoethyl)morpholine → (3aR,7S,10S,12R,24aR)-7-tert-butyl-N-[(1R,2S)-2-ethenyl-1-({[1-(methoxymethyl)cyclopropyl]sulfonyl}carbamoyl)cyclopropyl]-19-[2-(morpholin-4-yl)ethoxy]-5,8-dioxo-1,2,3,3a,5,6,7,8,11,12,20,21,22,23,24,24a-hexadecahydro-10H-9,12-methanocyclopenta[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-10-carboxamide

HRID 522385Notes

Reaction equation

HRID 522385 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[C:10]([C@H:14]1[C:41](=[O:42])[N:40]2[CH2:43][C@@H:37]([CH2:38][C@H:39]2[C:44]([NH:46][C@:47]2([C:52](=[O:63])[NH:53][S:54]([C:57]3([CH2:60][O:61][CH3:62])[CH2:59][CH2:58]3)(=[O:56])=[O:55])[CH2:49][C@H:48]2[CH:50]=[CH2:51])=[O:45])[O:36][C:26]2=[N:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=3[C:34]([OH:35])=[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]2[CH2:64][CH2:65][CH2:66][C@H:18]2[O:17][C:16](=[O:67])[NH:15]1)([CH3:13])([CH3:12])[CH3:11]>>[C:10]([C@H:14]1[C:41](=[O:42])[N:40]2[CH2:43][C@@H:37]([CH2:38][C@H:39]2[C:44]([NH:46][C@:47]2([C:52](=[O:63])[NH:53][S:54]([C:57]3([CH2:60][O:61][CH3:62])[CH2:59][CH2:58]3)(=[O:55])=[O:56])[CH2:49][C@H:48]2[CH:50]=[CH2:51])=[O:45])[O:36][C:26]2=[N:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=3[C:34]([O:35][CH2:2][CH2:3][N:4]3[CH2:9][CH2:8][O:7][CH2:6][CH2:5]3)=[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]2[CH2:64][CH2:65][CH2:66][C@H:18]2[O:17][C:16](=[O:67])[NH:15]1)([CH3:11])([CH3:12])[CH3:13]

Participants

3

Reactant 2

HCID 15021014-(2-Bromoethyl)morpholineHCID 178455698HCID 178455698, compound

Product 1

HCID 117599009(3aR,7S,10S,12R,24aR)-7-tert-butyl-N-[(1R,2S)-2-ethenyl-1-({[1-(methoxymethyl)cyclopropyl]sulfonyl}carbamoyl)cyclopropyl]-19-[2-(morpholin-4-yl)ethoxy]-5,8-dioxo-1,2,3,3a,5,6,7,8,11,12,20,21,22,23,24,24a-hexadecahydro-10H-9,12-methanocyclopenta[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-10-carboxamide

Procedure

The title compound was prepared using the same method as described for Example 42 using 4-(2-bromoethyl)morpholine and (3aR,7S,10S,12R,24aR)-7-tert-butyl-N-[(1R,2S)-2-ethenyl-1-({[1-(methoxymethyl)cyclopropyl]sulfonyl}carbamoyl)cyclopropyl]-19-hydroxy-5,8-dioxo-1,2,3,3a,5,6,7,8,11,12,20,21,22,23,24,24a-hexadecahydro-10H-9,12-methanocyclopenta[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-10-carboxamide (Example 35). Purification by flash chromatography (ISCO) afforded the desired product (21.5 mg). LRMS (ES+) m/z 937.3 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customPurification by flash chromatography (ISCO)

Sources & evidence

ORD record
ord-9d6773f1313f4ddaa9f6476d4eb82f59
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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