Hydrochloric Acid → HCID 12837209, compound

HRID 615346

Reaction equation

HRID 615346 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 12837209HCID 12837209, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a28c83ca718d4de8bf45702e3d24af4c
Source dataset
uspto-grants-1985_02
Patent number
US04499102

Linked notes

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