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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 1096844
Notes
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Reaction equation

HRID 1096844 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866370647-[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 6-ethyl ester

Product 1

HCID 866370687-[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 esterYield 56%

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

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

  1. temperaturecooled to rt
  2. customthe solvent removed in vacuo
  3. customThe crude mixture was partitioned between Et2O and aq. sat. NH4Cl
  4. extractionThe aq. layer was extracted once more with Et2O
  5. extractionextracted again with Et2O
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes