Sodium Hydroxide → 7-[2-(2-Hydroxyethoxymethyl)thiazol-5-yl]-3,9-diazabicyclo[3.3.1]-non-6-ene-3,6,9-tricarboxylic acid 3,9-di-tert-butyl ester

HRID 1096844Notes

Reaction equation

[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]2[N:26]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:13]([CH2:14][C:15]=1[C:16]1[S:20][C:19]([CH2:21][O:22][CH2:23][CH2:24][OH:25])=[N:18][CH:17]=1)[CH2:12][N:11]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:10]2)=[O:7])C>CCO>[C:37]([O:36][C:34]([N:11]1[CH2:10][CH:9]2[N:26]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:13]([CH2:14][C:15]([C:16]3[S:20][C:19]([CH2:21][O:22][CH2:23][CH2:24][OH:25])=[N:18][CH:17]=3)=[C:8]2[C:6]([OH:7])=[O:5])[CH2:12]1)=[O:35])([CH3:38])([CH3:39])[CH3:40]

Participants

Conditions

Temperature: 70 °C

Procedure

Aq. 1M NaOH (1.0 mL) was added to a sol. of the compound C5 (50 mg, 0.090 mmol) in EtOH (1.0 mL). The resulting mixture was stirred at 70° C. for 1 h, cooled to rt and the solvent removed in vacuo. The crude mixture was partitioned between Et2O and aq. sat. NH4Cl. The aq. layer was extracted once more with Et2O, then acidified to pH= 4-5, and extracted again with Et2O. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to yield the title compound (26.4 mg, 56%), which was not further purified. LC-MS: tR=0.82 min, ES+: 526.41.

Workup

temperaturecooled to rt
customthe solvent removed in vacuo
customThe crude mixture was partitioned between Et2O and aq. sat. NH4Cl
extractionThe aq. layer was extracted once more with Et2O
extractionextracted again with Et2O
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-ce56f1d0d28a4e2b96df3c93fecf2d8c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138340B2

Reaction notes

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