Hydrochloric Acid → HCID 53810310、化合物

HRID 263507

反応式

HRID 263507 の反応式
[C:1]([S:4][C@H:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@H:6]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]([O:9]C)=[O:8])(=O)[CH3:2].[OH-].[Na+].Br[C:28]1[CH:33]=C[CH:31]=[C:30](C)[C:29]=1[CH3:35].Cl.[CH3:37]O>>[CH3:37][C@:6]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])([C@H:5]([S:4][CH2:1][C:2]1[CH:31]=[CH:30][C:29]([CH3:35])=[CH:28][CH:33]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:7]([OH:9])=[O:8]

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 684723-Bromo-o-xyleneHCID 15747430HCID 15747430、化合物

生成物 1

HCID 53810310HCID 53810310、化合物収率 79%

実験手順

The acetylated thiol 17 (500 mg, 1.4 mmol) was dissolved in methanol (2 mL) and NaOH was added (1.6 mL, 1M aqueous), followed by bromoxilene (300 mg, 1.62 mmol). After 20 min most of the starting material has disappeared (monitored by TLC). The solution was carefully neutralized with dilute HCl. The volatiles were removed in vacuo and the residue was extracted with Cl2CH2 (3×) The organic layer was washed with brine and dried over Na2SO4. The crude product was purified by flash column chromatography (silica, 5% to 20% ethyl acetate/hexane) to give the desired ester 18 (480 mg, 79%) as a white solid, which crystallized. mp 97°-98° C. (ether-hexane); [α]20D =-171.8° (c=1.05, CHCl3); 1H NMR (CDCl3).δ1.384 (s, 9H), 2.326 (s, 3H), 3.393 (d, J=13 Hz, 1H), 3.551 (d, J=13 Hz, 1H), 3.572 (s, 3H, OCH3), 4.126 (d,J=5.4 Hz, H-3), 4.630 (dd, J=8.8, 5.8 Hz, 1H, H-2), 5.220 (bd, J=8.8 Hz, 1H, H--N), 7.028-7.107 (m, 4H), 7.291-7.362 (m, 5H); 13C NMR (CDCl3).δ21.0, 28.3, 35.5, 51.6, 52.1, 57.5, 80.1, 127.8, 128.5, 128.7, 128.9, 129.2, 134.3, 136.9, 138.4, 154.7, 170.8; MS m/z 316 [M+H]+ ; Anal. Calcd for C23H29O4NS.1/4H2O: C, 65.76; H, 7.08; N, 3.33. Found: C, 65.59; H, 7.03; N, 3.36.

後処理

  1. customThe volatiles were removed in vacuo
  2. extractionthe residue was extracted with Cl2CH2 (3×) The organic layer
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by flash column chromatography (silica, 5% to 20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-bb2a4022d2914891b745ddac85c139dd
出典データセット
uspto-grants-1997_07
特許番号
US05643872

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