Succinic anhydride → HCID 12837158, compound

HRID 615349Notes

Reaction equation

HRID 615349 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(N(CC)CC)C.[C:23]1(=[O:29])[O:28][C:26](=[O:27])[CH2:25][CH2:24]1>CC(C)=O>[C:26]([CH2:25][CH2:24][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:29])([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 2825745(4R)-2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid

Product 1

HCID 12837158HCID 12837158, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of (4R)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid (4.5 g) and triethylamine (4.0 g) in acetone (100 ml), succinic anhydride (2.0 g) was added at room temperature, and stirred for 3 hours at the same temperature. The reaction mixture was concentrated in vacuo, and acidified with dilute hydrochloric acid. The separated oil was extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give 4.9 g (75%) of the titled compound: mp 190°-191° C. (dec.) (ethyl acetate-methanol); [α]D27 +181.6° (c=1.0, methanol). IR (nujol, cm-1): 3210 (OH), 1720 (COOH), 1618 (CON), 1602 (aromatic), 1245, 1173, 940, 763. NMR (DMSO-6, δ): 2.0-2.7 (4H, m, --CH2CH2 --), 3.03 (1H, ABq (A part), d, J=11.0, 10.0 Hz, C5 --HA), 3.36 (1H, ABq (B part), d, J=11.0, 7.0 Hz, C5 --HB), 4.61 and 5.07 (1H, dd, J=10.0, 7.0 Hz and m, C4 --H), 6.36 (1H, s, C2 --H), 6.5-8.0 (4H, arom. H). TLC: Rf value* 0.35.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionThe separated oil was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-51b53ba6ac114adaa8d98b2efb8ff27c
Source dataset
uspto-grants-1985_02
Patent number
US04499102

Reaction notes

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