Hydrochloric Acid → HCID 12837137、化合物

HRID 615345

反応式

HRID 615345 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[NH:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9]1.[OH-:16].[Na+].[C:18](Cl)(=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](Cl)=[O:26].Cl>C(=O)([O-])[O-].[K+].[K+]>[C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([N:12]1[C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9][CH:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1])=[O:26])([OH:28])=[O:16]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 534653Octanedioyl dichlorideHCID 2825745(4R)-2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid

生成物 1

HCID 12837137HCID 12837137、化合物収率 61%

試薬・触媒・溶媒 1

HCID 11430Potassium Carbonate溶媒

実験手順

(4R)-2-(2-Hydroxyphenyl)-4-thiazolidinecarboxylic acid (6.8 g), in N sodium hydroxide (30 ml) and octanedioyl dichloride (6.3 g), were added dropwise to 1M potassium carbonate (60 ml) with stirring under ice-cooling. After the addition, the reaction mixture was stirred for 1 hour at the same temperature and for additional 1 hour at room temperature. The solution was acidified with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residual oil*2 was purified by silica gel column chromatography to give 7.0 g (61%) of the titled compound: mp 155°-157° C. (dec.) (ethyl acetate); [α]D27 +134.1° (c=0.5, methanol). IR (nujol, cm-1): 3220 (OH), 1710 (COOH), 1620 (CON), 1600 (aromatic), 1415, 1235, 1172, 950, 760. NMR (DMSO-d6,δ): 0.53-1.73 (8H, m, -- CH2 --CH2)4CH2 --), 1.77-2.57 (4H, m, --CH2 --CH2)4CH2 --), 3.03 (1H, ABq (A part), d, J=11.5, 8.5 Hz, C5*1 --HA), 3.37 (1H, ABq (B part), d, J=11.5, 6.5 Hz, C5 --HB), 4.60 (1H, dd, J=8.5, 6.5 Hz, C4 --H), 6.28 (1H, s, C2 --H), 6.45-8.07 (4H, m, arom. H), 9.77 (1H, s, C2 --H), 6.45-8.07 (4H, m, arom. H), 9.77 (1H, s, --COOH). TLC: Rf value*3 0.52. pyrrolidine ring. The same shall be applied hereinafter.

後処理

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe reaction mixture was stirred for 1 hour at the same temperature and for additional 1 hour at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residual oil*2 was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-1d3bde403eac4e73977fbb81c22d7767
出典データセット
uspto-grants-1985_02
特許番号
US04499102

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