Hydrogen chloride-ethyl acetate → Hydrochloric Acid

HRID 575076Notes

Reaction equation

HRID 575076 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([C:17]#[C:18][C:19]1[CH:20]=[CH:21][C:22]3[O:31][CH2:30][CH2:29][N:28]4[C:24](=[N:25][C:26]([C:32](=[O:34])[NH2:33])=[CH:27]4)[C:23]=3[CH:35]=1)([OH:16])[CH2:12]2)=O)(C)(C)C.[ClH:36].CCOC(C)=O>CO>[OH:16][C:11]1([C:17]#[C:18][C:19]2[CH:20]=[CH:21][C:22]3[O:31][CH2:30][CH2:29][N:28]4[CH:27]=[C:26]([C:32]([NH2:33])=[O:34])[N:25]=[C:24]4[C:23]=3[CH:35]=2)[CH2:10][C@H:9]2[NH:8][C@H:13]([CH2:14][CH2:15]2)[CH2:12]1.[ClH:36]

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 866931023-(2-Carbamoyl-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-9-ylethynyl)-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidYield 96%HCID 8669310310-(((1R,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-3-yl)ethynyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a solution of 3-(2-Carbamoyl-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-9-ylethynyl)-3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.5 g, 1.1 mmol) in methanol (20 mL) was added HCl/EtOAc (4 M, 20 mL) at 0° C. The solution was stirred for 3 h at room temperature. The reaction mixture was filtered and washed with EtOAc to afford desired product as HCl salt (400 mg, 96%). 1H NMR: (DMSO-d6, 400 MHz): δ 9.44 (s, 1H), 9.10 (s, 1H), 8.52 (s, 1H), 8.02 (s, 1H), 7.46 (s, 1H), 7.38 (d, J=8.8 Hz, 1H), 7.08 (d, J=8.4 Hz, 1H), 4.55 (s, 4H), 3.96 (s, 2H), 2.45-2.17 (m, 6H), 1.91-1.88 (m, 2H). LCMS [M+H]+=379.0.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with EtOAc

Sources & evidence

ORD record
ord-98988353348e459b93636f2840642499
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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