Water → HCID 68182986, compound

HRID 1615567Notes

Reaction equation

HRID 1615567 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[C:13]3[N:22]=[C:21]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[S:20][C:14]=3[C:15](=[O:19])[NH:16][CH2:17][CH:18]=2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].O>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[C:13]3[N:22]=[C:21]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[S:20][C:14]=3[C:15](=[O:19])[NH:16][CH2:17][CH:18]=2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68182899HCID 68182899, compound

Product 1

HCID 68182986HCID 68182986, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-chloro-2-[2-(morpholin-4-yl)-4-oxo-5,6-dihydro-4H-[1,3]thiazolo[5,4-c]azepin-8-yl]benzoate (0.125 g, 0.298 mmol) in THF (3.7 mL) and MeOH (1.2 mL) was added a solution of 1M sodium hydroxide in water (3.66 mL, 3.66 mmol). The solution was stirred at room temperature for 16 hours. The solvents were evaporated and the residue was diluted with water and then added 1N hydrogen chloride aqueous solution until pH 7 was reached. Extracted twice with EA and the combined organic layer was then washed with brine then dried over anhydrous sodium sulfate and concentrated to give the product (0.100 g, 83%) which was used directly in the next step. LCMS: (AA) ES+ 406, 408. 1H NMR (400 MHz, d6-DMSO) δ: 12.79 (s, 1H), 7.86 (t, J=4.9 Hz, 1H), 7.68 (d, J=2.4 Hz, 1H), 7.57 (dd, J=8.2, 2.4 Hz, 1H), 7.32 (d, J=8.2 Hz, 1H), 6.21 (t, J=6.9 Hz, 1H), 3.65-3.55 (m, 6H), 3.30-3.26 (m, 4H).

Workup

  1. customThe solvents were evaporated
  2. additionthe residue was diluted with water
  3. additionadded 1N hydrogen chloride aqueous solution until pH 7
  4. extractionExtracted twice with EA
  5. washthe combined organic layer was then washed with brine
  6. dry with materialthen dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bde469b07b7b413985d9768cbb39e954
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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