Water → HCID 11422118, 화합물

HRID 29672노트

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HRID 29672 반응식
C[O:2][C:3](=[O:44])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14]/[N:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=2)=[CH:6][C:5]=1[NH:27][C:28](=[O:43])[C:29]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=1.[OH-].[Na+].O>C(O)C>[F:36][C:35]([F:37])([F:38])[C:33]1[CH:34]=[C:29]([CH:30]=[C:31]([C:39]([F:41])([F:40])[F:42])[CH:32]=1)[C:28]([NH:27][C:5]1[CH:6]=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14]/[N:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:24])([CH3:25])[CH3:26])=[CH:19][CH:18]=2)[CH:8]=[CH:9][C:4]=1[C:3]([OH:44])=[O:2])=[O:43]

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 87733702methyl 2-[[3,5-bis(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-(4-tert-butylphenyl)methylideneamino]oxypropoxy]benzoate

생성물 1

HCID 11422118HCID 11422118, 화합물수율 45%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution 2-{[3,5-bis(trifluoromethyl)benzoyl]amino}-4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid methyl ester (0.30 g, 0.48 mmol) in ethanol (20 mL) was added 1.0 N, sodium hydroxide solution (4 mL). This mixture was heated to reflux for 20 minutes and then allowed to cool back to room temperature. Water (5 mL) was added to the mixture, it was concentrated to approximately ¼ volume and then partitioned between ethyl acetate and water. The aqueous layer was acidified to approximately pH 3 using 1 N hydrochloric acid. The layers were then separated. The aqueous layer was extracted with two additional portions of ethyl acetate. The organics were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography through silica gel using ethyl acetate/hexanes (10/90 with 1% formic acid gradient to 20/80 with 1% formic acid) and then recrystallized one time from chloroform/hexanes (1/20) to give 2-{[3,5-bis(trifluoromethyl)benzoyl]amino}-4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid (0.13 g, 45%) as a white powder. mp=157.5-158.5° C. 1H NMR (500 MHz, DMSO-d6); δ 13.54 (bs, 1H), 12.54 (s, 1H), 8.51 (s, 2H), 8.45 (s, 1H), 8.32 (d, 1H), 8.21 (s, 1H), 8.00 (d, 1H), 7.50-7.37 (AA′BB′, 4H), 6.83 (dd, 1H), 4.27 (t, 2H), 4.21 (t, 2H), 2.16 (m, 2H), 1.23 (s, 9H). Mass spec (MW 610.55); (ES−) m/z 609.2. Elemental analysis; Calculated for C30H28F6N2O5: C, 59.02; H, 4.62; N, 4.59. Found: C, 58.78; H, 4.52; N, 4.46.

후처리

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 20 minutes
  3. concentrationwas concentrated to approximately ¼ volume
  4. custompartitioned between ethyl acetate and water
  5. customThe layers were then separated
  6. extractionThe aqueous layer was extracted with two additional portions of ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was purified by flash chromatography through silica gel
  11. customrecrystallized one time from chloroform/hexanes (1/20)

출처 및 근거

ORD 기록
ord-af45f909c9f042d5b38afe82f0c8ee70
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420083B2

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