Hydrochloric Acid → HCID 12837137, 화합물

HRID 615345

반응식

HRID 615345 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 12837137HCID 12837137, 화합물수율 61%

시약·촉매·용매 1

HCID 11430Potassium Carbonate용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-1d3bde403eac4e73977fbb81c22d7767
출처 데이터셋
uspto-grants-1985_02
특허 번호
US04499102

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