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

HRID 1454201노트

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HRID 1454201 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a0a0d43ea996471cb81adf54c338d841
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476764B2

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