Citric Acid → HCID 86589687、化合物

HRID 2217635

反応式

HRID 2217635 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 86589687HCID 86589687、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9fcb1e0df5cc4db589d0e5f590873e5e
出典データセット
uspto-grants-2008_08
特許番号
US07407978B2

関連ノート

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