Hydrochloric Acid → Hydrochloric Acid

HRID 1429074Notes

Reaction equation

HRID 1429074 reaction equation
[CH:1]1([S:4]([NH:7][C:8]([C@@:10]23[CH2:25][C@H:24]2[CH2:23][C:22]([F:27])([F:26])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]([NH:28]C(=O)OC(C)(C)C)[C:15](=[O:36])[N:14]2[CH2:37][C@H:38]([O:40][C:41]4[CH:50]=[N:49][C:48]5[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=5)[N:42]=4)[CH2:39][C@H:13]2[C:12](=[O:51])[NH:11]3)=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[ClH:52]>C(OCC)(=O)C>[NH2:28][C@@H:16]1[C:15](=[O:36])[N:14]2[CH2:37][C@H:38]([O:40][C:41]3[CH:50]=[N:49][C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[N:42]=3)[CH2:39][C@H:13]2[C:12](=[O:51])[NH:11][C@:10]2([C:8]([NH:7][S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:6])=[O:5])=[O:9])[CH2:25][C@H:24]2[CH2:23][C:22]([F:26])([F:27])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[ClH:52]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68008833HCID 68008833, compound

Product 2

HCID 313Hydrochloric AcidYield 1,839.9%HCID 68008839HCID 68008839, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To tert-butyl (2R,6S,13aS,14aR,16aS)-14a-(cyclopropylsulfonylcarbamoyl)-12,12-difluoro-5,16-dioxo-2-(quinoxalin-2-yloxy)octadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-ylcarbamate (Example 1, 8.81 mg, 0.012 mmol) was added ethyl acetate (60 μl) followed by HCl (4 N in dioxane, 60 μl, 0.240 mmol). The solution was stirred at room temperature for 4 hr (a solid appeared), and LC/MS showed completion. The reaction mixture was concentrated to give the title compound (2R,6S,13aS,14aR,16aS)-6-amino-N-(cyclopropylsulfonyl)-12,12-difluoro-5,16-dioxo-2-(quinoxalin-2-yloxy)octadecahydrocyclo propa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxamide, hydrochloric acid (8.05 mg, quantitative yield).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-761a2dae6a0f4f039420f426d16489f6
Source dataset
uspto-grants-2015_01
Patent number
US08937041B2

Reaction notes

Loading…