Hydrochloric Acid → HCID 86683282, compound

HRID 1852293Notes

Reaction equation

HRID 1852293 reaction equation
[F:1][CH2:2][C:3]1([S:6]([NH:9][C:10]([C@@:12]23[CH2:27][C@H:26]2[CH:25]=[CH:24][CH2:23][CH2:22][C@@H:21]([CH3:28])[CH2:20][C@@H:19]([CH3:29])[C@H:18]([NH:30]C(=O)OC(C)(C)C)[C:17](=[O:38])[N:16]2[CH2:39][C@H:40]([O:42][C:43]4[CH:52]=[N:51][C:50]5[C:45](=[CH:46][C:47]([O:53][CH3:54])=[CH:48][CH:49]=5)[N:44]=4)[CH2:41][C@H:15]2[C:14](=[O:55])[NH:13]3)=[O:11])(=[O:8])=[O:7])[CH2:5][CH2:4]1.[ClH:56]>O1CCOCC1>[ClH:56].[NH2:30][C@@H:18]1[C:17](=[O:38])[N:16]2[CH2:39][C@H:40]([O:42][C:43]3[CH:52]=[N:51][C:50]4[C:45](=[CH:46][C:47]([O:53][CH3:54])=[CH:48][CH:49]=4)[N:44]=3)[CH2:41][C@H:15]2[C:14](=[O:55])[NH:13][C@:12]2([C:10]([NH:9][S:6]([C:3]3([CH2:2][F:1])[CH2:5][CH2:4]3)(=[O:8])=[O:7])=[O:11])[CH2:27][C@H:26]2[CH:25]=[CH:24][CH2:23][CH2:22][C@@H:21]([CH3:28])[CH2:20][C@H:19]1[CH3:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71005501tert-butyl ((2R,6S,7R,9R,13aS,14aR,16aS,Z)-14a-(((1-(fluoromethyl)cyclopropyl)sulfonyl)carbamoyl)-2-((7-methoxyquinoxalin-2-yl)oxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate

Product 1

HCID 86683282HCID 86683282, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl ((2R,6S,7R,9R,13aS,14aR,16aS,Z)-14a-(((1-(fluoromethyl)cyclopropyl)sulfonyl)carbamoyl)-2-((7-methoxyquinoxalin-2-yl)oxy)-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate (120 mg, 0.15 mmol) in 4M HCl in dioxane (10 ml 4 M solution) was stirred at room temperature for 2 h. The solvent was evaporated under reduced pressure to get crude compound (100 mg, 95%) as brown solid. The crude compound was washed with diethyl ether and taken to the next step without further purification. 1H NMR (400 MHz, CD3OD): δ ppm 9.19 (s, 1H) 8.26-8.34 (m, 2H) 7.90 (d, J=8.78 Hz, 2H) 7.26-7.34 (m, 3H) 6.02 (br. s., 1H) 5.58-5.67 (m, 1H) 5.04 (t, J=9.54 Hz, 1H) 4.59-4.71 (m, 2H) 4.33-4.53 (m, 1H) 4.12-4.26 (m, 2H) 3.98 (s, 3H) 3.73-3.81 (m, 2H) 3.66-3.71 (m, 2H) 2.77-2.97 (m, 2H) 2.42-2.75 (m, 3H) 1.91-2.11 (m, 2H) 1.67-1.78 (m, 2H) 1.44-1.62 (m, 2H) 1.21-1.42 (m, 5H) 1.01-1.15 (m, 5H) 0.92 (br. s., 1H): MS: MS m/z 687.4 (M+−36).

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-28435d6d1c4b4f92acd58fa9cd877024
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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