Methanol → 3-Acetyl-5-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-benzoic acid

HRID 1454201Notes

Reaction equation

HRID 1454201 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][S:11]2(=[O:17])=[O:16])[CH:7]=[C:6]([C:18](=[O:20])[CH3:19])[CH:5]=1.CO.O.[Li+].[OH-]>C1COCC1>[C:18]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][S:11]2(=[O:16])=[O:17])[CH:7]=1)[C:3]([OH:21])=[O:2])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 575293353-Acetyl-5-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-benzoic acid methyl ester

Product 1

HCID 575293073-Acetyl-5-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-benzoic acidYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-acetyl-5-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-benzoic acid methyl ester (100 mg, 0.32 mmol) in a mixture of THF (0.3 mL), MeOH (0.6 mL) and H2O (1.5 mL) was added LiOH (23.1 mg, 0.96 mmol) and the mixture was stirred at room temperature for 1 h. The mixture was concentrated and partitioned between ethyl acetate and H2O. The aqueous layer was washed with ethyl acetate twice and acidified with 1N HCl solution to pH around 2˜3. The aqueous layer was extracted with ethyl acetate 3 times and the combined organic layers were dried over sodium sulfate and concentrated under vacuum to give the title compound (93 mg): 1H NMR (CD3OD, 500 MHz) δ ppm 1.93-1.99 (2H, m), 2.31-2.37 (2H, m), 2.67 (3H, s), 3.27-3.30 (2H, m), 3.83 (2H, t, J=5 Hz), 8.13 (1H, m), 8.20 (1H, m), 8.52 (1H, m). HPLC retention time: 1.292 min (method A). MS (ESI) (M+Na)+ 320.14.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and H2O
  3. washThe aqueous layer was washed with ethyl acetate twice
  4. extractionThe aqueous layer was extracted with ethyl acetate 3 times
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a0a0d43ea996471cb81adf54c338d841
Source dataset
uspto-grants-2009_01
Patent number
US07476764B2

Reaction notes

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