Sodium Hydroxide → HCID 69675345, compound

HRID 2406410Notes

Reaction equation

HRID 2406410 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:34])[CH:7]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:8]1[C:9]([CH3:28])=[N:10][C:11]2[S:12][C:13]3[CH2:14][O:15][CH2:16][CH2:17][C:18]=3[C:19]=2[C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)C>C(O)C.O1CCCC1>[C:30]([O:29][CH:7]([C:8]1[C:9]([CH3:28])=[N:10][C:11]2[S:12][C:13]3[CH2:14][O:15][CH2:16][CH2:17][C:18]=3[C:19]=2[C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[C:6]([OH:34])=[O:5])([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69672878HCID 69672878, compound

Product 1

HCID 69675345HCID 69675345, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Aqueous sodium hydroxide (2N, 2 mL, 4 mmol) was added to a stirred solution of tert-Butoxy-(2-methyl-4-p-tolyl-5,8-dihydro-6H-7-oxa-9-thia-1-aza-fluoren-3-yl)-acetic acid ethyl ester (66 mg, 0.15 mmol) in ethanol (2 mL) and tetrahydrofuran (2 mL) and the reaction was stirred for 2 hours at 60° C. The reaction was concentrated in vacuo until only the aqueous remained. The pH was adjusted to 2 by the addition of 2N aqueous HCl. The resulting solid was collected by filtration and purified by preparative HPLC to afford the title compound. LCMS 3.63 min, ES+/AP+ 425.1 (MH+).

Workup

  1. concentrationThe reaction was concentrated in vacuo until only the
  2. additionThe pH was adjusted to 2 by the addition of 2N aqueous HCl
  3. filtrationThe resulting solid was collected by filtration
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-dabc8de6e71640b3bc180ee948c36935
Source dataset
uspto-grants-2014_08
Patent number
US08809363B2

Reaction notes

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