Methanol → 3-[4-(Azetidine-1-carbonyl)phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acid

HRID 600540노트

반응식

HRID 600540 반응식
[N:1]1([C:5]([C:7]2[CH:31]=[CH:30][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]4[CH2:27][CH2:26][N:25]([CH3:28])[C:24]4=[O:29])[CH:21]=3)[C:15]([O:17]C)=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.CO.O>C1COCC1.[OH-].[Li+]>[N:1]1([C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]4[CH2:27][CH2:26][N:25]([CH3:28])[C:24]4=[O:29])[CH:21]=3)[C:15]([OH:17])=[O:16])=[CH:30][CH:31]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 887MethanolHCID 962WaterHCID 59761134Methyl 3-[4-(azetidine-1-carbonyl)phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate2회

생성물 1

HCID 597611473-[4-(Azetidine-1-carbonyl)phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acid수율 100%

시약·촉매·용매 2

HCID 3939Lithium Hydroxide용매HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 3-[4-(azetidine-1-carbonyl)phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate (Intermediate 16) (309 mg, 0.73 mmol) was dissolved in THF (6 mL) and methanol (2 mL) and IN lithium hydroxide (0.88 mL) was added followed by water (8 mL). The resultant solution was stirred for 1 hr at room temperature. The majority of the organic solvent was removed by distillation under reduced pressure. The remaining aqueous solution was filtered and acidified with 2N hydrochloric acid and extracted with ethyl acetate (2×40 mL), the combined organics were washed with water (10 mL) and brine (20 mL) and dried (MgSO4) to afford the product (298 mg, 100%). m/z 411 (M+H)+

후처리

  1. customThe majority of the organic solvent was removed by distillation under reduced pressure
  2. filtrationThe remaining aqueous solution was filtered
  3. extractionextracted with ethyl acetate (2×40 mL)
  4. washthe combined organics were washed with water (10 mL) and brine (20 mL)
  5. dry with materialdried (MgSO4)

출처 및 근거

ORD 기록
ord-a813d9ae9d4c47f388076d702fc4dfa0
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902200B2

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