Hydrochloric Acid → HCID 12837209, 화합물

HRID 615346

반응식

HRID 615346 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.[C:16](Cl)(=[O:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24].Cl>C(=O)([O-])[O-].[K+].[K+]>[C:16]([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])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([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:24]

참가 물질

5

반응물 3

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

생성물 1

HCID 12837209HCID 12837209, 화합물수율 86%

시약·촉매·용매 1

HCID 11430Potassium Carbonate용매

실험 절차

To a stirred solution of (4R)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid (6.8 g) in 1M potassium carbonate (45 ml), octanedioyl dichloride (3.2 g) was added dropwise 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, 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 was purified by silica gel column chromatography to give 7.6 g (86%) of the titled compound: mp 93°-97° C. (dec.); [α]D27 +123.6° (c=0.5, methanol). IR (nujol, cm-1): 1720 (COOH), 1620 (CON), 1600 (aromatic), 1230, 1090, 855, 765. NMR (CD3OD) δ: 0.7-1.7 (8H, m, --CH2 --CH2)4CH2 --), 1.8-2.4 (4H, m, --CH2 --CH2)4CH2), 3.25 (4H, d, J=7.5 Hz, C5 --H), 4.81 (2H, t, J=7.5 Hz, C4 --H), 6.35 (2H, s, C2 --H), 6.7-8.0 (8H, m, arom. H). TLC: Rf value* 0.34.

후처리

  1. temperaturecooling
  2. additionAfter the addition
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residual oil was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a28c83ca718d4de8bf45702e3d24af4c
출처 데이터셋
uspto-grants-1985_02
특허 번호
US04499102

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