Sodium Hydroxide → 3-[5-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoic acid

HRID 2189811ノート

反応式

HRID 2189811 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[N:23]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[N:22]=[CH:21]4)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+]>C(O)C.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[N:23]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[N:22]=[CH:21]4)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 59316802Ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoate

生成物 1

HCID 250625593-[5-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoic acid収率 28.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

Ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoate (D58) (523 mg, 1.17 mmol) was dissolved in mixture of ethanol (20 ml) and THF (10 ml) by warming at 50° C. Cooled to RT and added 2N NaOH (1 ml, 2 mmol) and left standing at RT for 30 minutes. Evaporated off the solvent, added water (50 ml) and washed with EtOAc (50 ml). Acidified aqueous layer and extracted product into EtOAc (50 ml). The EtOAc layer was dried (MgSO4) and the solvent evaporated. Triturating with diethyl ether gave the title compound (139 mg) as a beige solid. δH (d6-DMSO, 400 MHz): 1.39 (6H, d), 2.90 (2H, t), 4.66 (2H, t), 4.94-5.03 (1H, m), 7.57 (1H, d), 7.90 (1H, d), 8.07 (1H, dd), 8.28 (1H, d), 8.42 (1H, dd), 8.54 (2H, dd), 12.35 (1H, broad s). MS (ES): C22H19N5O4 requires 417; found (MH+) 418.

後処理

  1. temperatureCooled to RT
  2. waitleft
  3. customEvaporated off the solvent
  4. additionadded water (50 ml)
  5. washwashed with EtOAc (50 ml)
  6. extractionAcidified aqueous layer and extracted product into EtOAc (50 ml)
  7. dry with materialThe EtOAc layer was dried (MgSO4)
  8. customthe solvent evaporated
  9. customTriturating with diethyl ether

出典と根拠

ORDレコード
ord-1c3015aebecb419790a75b2d39763f32
出典データセット
uspto-grants-2012_12
特許番号
US08324254B2

反応ノート

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