Citric Acid → HCID 86589687, 화합물

HRID 2217635

반응식

HRID 2217635 반응식
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1)[CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[O:38]=[C:39]1[NH:43][C:42](=[O:44])[CH:41]([CH2:45][C:46]2[CH:60]=[CH:59][C:49]([O:50][C:51]3[CH:58]=[CH:57][C:54]([CH:55]=O)=[CH:53][CH:52]=3)=[CH:48][CH:47]=2)[S:40]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:31][O:30][C:28]1[CH:27]=[C:6]([CH:7]=[CH:55][C:54]2[CH:53]=[CH:52][C:51]([O:50][C:49]3[CH:59]=[CH:60][C:46]([CH2:45][CH:41]4[S:40][C:39](=[O:38])[NH:43][C:42]4=[O:44])=[CH:47][CH:48]=3)=[CH:58][CH:57]=2)[CH:5]=[C:4]([O:3][CH3:2])[CH:29]=1

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 10962038(3,5-Dimethoxybenzyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 597682934-[4-(2,4-Dioxothiazolidin-5-ylmethyl)-phenoxy]-benzaldehyde

생성물 1

HCID 86589687HCID 86589687, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a suspension of 3,5-dimethoxybenzyltriphenylphosphonium bromide (0.82 g, 2.0 mmol) in THF (10 mL) at 0° C. was added solid potassium tert-butoxide (224 mg, 2.0 mmol). The resultant red solution was stirred for 15 min at 0° C. then cooled to −78° C. Solid 53 (0.3 mg, 0.90 mmol) was added and the reaction was allowed to warm to room temperature. After 30 min 10% citric acid (50 mL) was added and the mixture was partitioned between water (50 mL) and ethyl acetate (75 mL). The organic layer was washed with water (50 mL) and brine (50 mL) then dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using hexanes-ethyl acetate (7:3) to yield 55 as a slightly opaque film (25 mg, 6%) after concentration and drying under high vacuum. 1H NMR (400 MHz, DMSO-d6): δ 12.04 (b s, 1H), 7.26 (d, J=8.8 Hz, 2H), 7.25 (d, J=8.8 Hz, 2H), 6.93 (d, J=8.4 Hz, 2H), 6.91 (d, J=8.4 Hz, 2H), 6.61 (d, J=12.4 Hz, 1H), 6.53 (d, J=12.0 Hz, 1H), 6.39 (d, J=2.4 Hz, 1H), 6.36 (t, J=2.4 Hz, 1H), 4.90 (dd, J=9.2 and 4.4 Hz, 1H), 3.62 (s, 6H), 3.36 (dd, J=14.0 and 4.4 Hz, 1H), 3.11 (dd, J=14.4, 8.8 Hz, 1H).

후처리

  1. temperaturethen cooled to −78° C
  2. temperatureto warm to room temperature
  3. customthe mixture was partitioned between water (50 mL) and ethyl acetate (75 mL)
  4. washThe organic layer was washed with water (50 mL) and brine (50 mL)
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-9fcb1e0df5cc4db589d0e5f590873e5e
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407978B2

연결된 노트

불러오는 중…