Hydrochloric Acid → HCID 69974596, compound

HRID 433672Notes

Reaction equation

HRID 433672 reaction equation
[OH-].[Na+].O1CCOCC1.[CH2:9]([O:11][C:12](=[O:42])[C:13]([NH:38][C:39](=[O:41])[CH3:40])([CH2:19][C:20]1[O:24][N:23]=[C:22]([CH:25]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26][CH:27]([CH3:29])[CH3:28])[CH:21]=1)[C:14]([O:16]CC)=[O:15])[CH3:10].Cl>C(OCC)(=O)C>[CH2:9]([O:11][C:12](=[O:42])[C:13]([NH:38][C:39](=[O:41])[CH3:40])([CH2:19][C:20]1[O:24][N:23]=[C:22]([CH:25]([NH:30][C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:26][CH:27]([CH3:29])[CH3:28])[CH:21]=1)[C:14]([OH:16])=[O:15])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20610268HCID 20610268, compound

Product 1

HCID 69974596HCID 69974596, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydroxide, 1N, (20.5 mL, 20.5 mmol, 1.10 equivalents) was added to a dioxane solution of 2-acetylamino-2-[3-(1-tert-butoxycarbonylamino-3-methyl-butyl)-isoxazol-5-ylmethyl]-malonic acid diethyl ester (8.99 g, 18.6 mmol, 1.0 equivalents) at room temperature over 30 minutes and the reaction was stirred overnight. The reaction was diluted with ethyl acetate (200 mL) and acidified to pH=1-1.5 with 1 N hydrochloric acid. The organic portion was washed with brine (200 mL) and dried over sodium sulfate. The solvent was removed in vacuo to give 8.589 of a 1:1 mixture (by 1H NMR) of 2-Acetylamino-2-[3-(1-tert-butoxycarbonylamino-3-methyl-butyl)-isoxazol-5-ylmethyl]-malonic acid monoethyl ester [MS (Cl) m/z 356.3 (M-99)] and the decarboxylated title compound [MS (CI) m/z 412.3 (M+1), 312.2 (M-99), 410.3(M−1)].

Workup

  1. washThe organic portion was washed with brine (200 mL)
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-480825dcd8974562993f93f064397aac
Source dataset
uspto-grants-2003_12
Patent number
US06667331B2

Reaction notes

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