Hydrochloric Acid → HCID 73055430, compound

HRID 1055460Notes

Reaction equation

HRID 1055460 reaction equation
Cl.O1CCOCC1.[F:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[C:14](=[O:20])[CH:13]=[C:12]2[CH2:21][N:22]1[C:28](=[O:29])[C@@H:27]([NH:30][C:31](=[O:43])[C@@H:32]([N:34](C)[C:35](=O)OC(C)(C)C)[CH3:33])[CH2:26][O:25][C:24]2[CH:44]=[CH:45][CH:46]=[CH:47][C:23]1=2>C([O-])(O)=O.[Na+]>[F:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[C:14](=[O:20])[CH:13]=[C:12]2[CH2:21][N:22]1[C:28](=[O:29])[C@@H:27]([NH:30][C:31](=[O:43])[C@@H:32]([NH:34][CH3:35])[CH3:33])[CH2:26][O:25][C:24]2[CH:44]=[CH:45][CH:46]=[CH:47][C:23]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131736362HCID 131736362, compound

Product 1

HCID 73055430HCID 73055430, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 3 M HCl in dioxane (36.0 g, 30 mL, 120 mmol, Eq: 1660) and tert-butyl (S)-1-((S)-5-((6-fluoro-1-methyl-2-oxo-1,2-dihydroquinolin-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (40 mg, 72.4 μmol, Eq: 1.00) were stirred at RT overnight. The mixture was diluted with sat. NaHCO3 and extracted with DCM The combined extracts were washed with H2O and concentrated. The residue was purified was purified by preparative TLC to give the title compound (26 mg, 95%) as a white solid. MS m/z 453 (MH+)

Workup

  1. extractionextracted with DCM The combined extracts
  2. washwere washed with H2O
  3. concentrationconcentrated
  4. customThe residue was purified
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-75d3d7de5c164e7fa4e0ee1553dbf674
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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