Hydrochloric Acid → HCID 67951394, compound

HRID 2401421Notes

Reaction equation

HRID 2401421 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]3[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=3[C:9](=[O:20])[NH:10][C@@H:11]([CH2:12][C:13]([O:15][C:16](C)(C)C)=[O:14])[C:5]=2[O:4][N:3]=1.Cl>CO>[CH3:1][C:2]1[C:6]2[C:7]3[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=3[C:9](=[O:20])[NH:10][C@@H:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:5]=2[O:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67971455HCID 67971455, compound

Product 1

HCID 67951394HCID 67951394, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a re-sealable vial containing a solution of tert-butyl 2-((4S)-1-methyl-6-oxo-5,6-dihydro-4H-benzo[c]isoxazolo[4,5-e]azepin-4-yl)acetate (1.04 g, 3.17 mmol) in MeOH (10 mL) was added hydrochloric acid (0.792 mL, 3.17 mmol, 4 M in 1,4-dioxane). After complete addition of reagents the reaction mixture was allowed to age until complete consumption of the carboxylic acid was detected by LC-MS. After ˜24 h, the reaction mixture was cooled to room temperature and concentrated in vacuo to give yellow solids. The solids were purified on Biotage system (gradient elution 5% EtOAc:1% i-PrOH:94% Hexanes to 80% EtOAc:1% i-PrOH:19% Hexanes) to give the titled product methyl 2-((4S)-1-methyl-6-oxo-5,6-dihydro-4H-benzo[c]isoxazolo[4,5-e]azepin-4-yl)acetate (0.500 g, 1.747 mmol, 55.1% yield) as white crystalline solids. LC/MS m/z 287 [M+H]+.

Workup

  1. additionAfter complete addition of reagents the reaction mixture
  2. customwas allowed to age until complete consumption of the carboxylic acid
  3. concentrationconcentrated in vacuo
  4. customto give yellow solids
  5. customThe solids were purified on Biotage system (gradient elution 5% EtOAc:1% i-PrOH:94% Hexanes to 80% EtOAc:1% i-PrOH:19% Hexanes)

Sources & evidence

ORD record
ord-4129ffaae9434aed97cf499df21ae909
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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