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Hydrochloric Acid → HCID 67682542, compound

HRID 1751590
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Reaction equation

HRID 1751590 reaction equation
[CH3:1][C:2]1([CH3:32])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([C@@H:17]4[C@@H:22]5[CH2:23][C@@H:19]([CH2:20][CH2:21]5)[N:18]4C(OC(C)(C)C)=O)[NH:14][C:13]=3[CH:31]=2)[O:3]1.Cl.O1CCOCC1.[CH3:40][O:41][C:42]([NH:44][C@@H:45]([CH:49]([CH3:51])[CH3:50])[C:46](O)=[O:47])=[O:43].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C.CO>[CH3:50][CH:49]([CH3:51])[C@H:45]([NH:44][C:42](=[O:43])[O:41][CH3:40])[C:46](=[O:47])[N:18]1[C@H:17]([C:15]2[NH:14][C:13]3[CH:31]=[C:9]([B:4]4[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:32])([CH3:1])[O:3]4)[CH:10]=[CH:11][C:12]=3[N:16]=2)[C@@H:22]2[CH2:23][C@H:19]1[CH2:20][CH2:21]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid
HCID 67506198
(1R,3S,4S)-tert-butyl 3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 67682542HCID 67682542, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (1R,3S,4S)-tert-butyl 3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (1.0 g, 2.3 mmol), methanol (10 mL), and 4M HCl in dioxane (11 mL, 44 mmol) was stirred at room temperature. The reaction was thoroughly concentrated after one hour. The resulting residue was dissolved in dimethylformamide (11.4 mL). To this solution was added (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (419 mg, 2.4 mmol) and HATU (909 mg, 2.4 mmol). Diisopropylethylamine (1.4 mL, 8.1 mmol) was added and the reaction was stirred at room temperature. After thirty minutes, the reaction was diluted with ethyl acetate. The organic phase was washed with water and brine, dried (Na2SO4) and concentrated. The crude material was purified by flash column chromatography to yield methyl (S)-3-methyl-1-oxo-1-((1R,3S,4S)-3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)butan-2-ylcarbamate (1.08 g, 95%).

Workup

  1. concentrationThe reaction was thoroughly concentrated after one hour
  2. dissolutionThe resulting residue was dissolved in dimethylformamide (11.4 mL)
  3. waitAfter thirty minutes
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by flash column chromatography

Sources & evidence

ORD record
ord-200df816b9cc4cc6ad19be0895bed063
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09156823B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes