Succinic anhydride → HCID 12837158, 화합물

HRID 615349

반응식

HRID 615349 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(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]

참가 물질

5

반응물 3

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

생성물 1

HCID 12837158HCID 12837158, 화합물수율 75.4%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-51b53ba6ac114adaa8d98b2efb8ff27c
출처 데이터셋
uspto-grants-1985_02
특허 번호
US04499102

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