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Propionic Acid → 4-Chloro-6-methyl-10,10-dioxo-2-propionylamino-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1173348
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HRID 1173348 반응식
C(Cl)(=O)C(Cl)=O.[C:7](O)(=[O:10])[CH2:8][CH3:9].[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18]([CH3:35])[C:19]2[O:25][C:24]3[C:26]([Cl:31])=[CH:27][C:28]([NH2:30])=[CH:29][C:23]=3[CH2:22][S:21](=[O:33])(=[O:32])[C:20]=2[CH:34]=1)=[O:15]>ClCCl.CN(C=O)C>[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18]([CH3:35])[C:19]2[O:25][C:24]3[C:26]([Cl:31])=[CH:27][C:28]([NH:30][C:7](=[O:10])[CH2:8][CH3:9])=[CH:29][C:23]=3[CH2:22][S:21](=[O:33])(=[O:32])[C:20]=2[CH:34]=1)=[O:15]
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참가 물질

6

반응물 3

HCID 1032Propionic AcidHCID 65578Oxalyl chlorideHCID 115596902-Amino-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda *6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

생성물 1

HCID 117045214-Chloro-6-methyl-10,10-dioxo-2-propionylamino-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 6344Dichloromethane용매

실험 절차

A solution of oxalyl chloride (0.17 mL, 2.03 mmol) and propionic acid (0.15 mL, 2.03 mmol) in dichloromethane (20 mL) was stirred for 1 h. Compound of Example 1 (0.5 g, 1.35 mmol) in DMF (5 mL) was added to the reaction mixture at 25° C. and stirred for 18 h. The solvent was removed under vacuum, water (25 mL) was added and the solid precipitated was filtered. The crude product was purified by column chromatography (silica gel, 1% methanol in chloroform) to obtain the title compound. Yield: 0.28 g, (60%); mp: 226-228° C.; 1H NMR (DMSO-d6, 300 MHz): δ 1.06 (t, 3H, CH3), 2.33 (q, 2H, CH2), 2.64 (s, 3H, CH3), 3.85 (s, 3H, OCH3), 5.30 (s, 2H, CH2), 7.66 (d, 1H, Ar), 7.88 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.15 (s, 1H, Ar), 10.26 (s, 1H, NH); MS: m/e (EI) 423 (M+); analysis: C19H18ClNO6S requires C, 53.66; H, 4.28; N, 3.30; Cl, 8.32; S, 7.56. found: C, 53.38; H, 4.27; N, 3.48; Cl, 8.64; S, 7.75%.

후처리

  1. customThe solvent was removed under vacuum, water (25 mL)
  2. additionwas added
  3. customthe solid precipitated
  4. filtrationwas filtered
  5. customThe crude product was purified by column chromatography (silica gel, 1% methanol in chloroform)

출처 및 근거

ORD 기록
ord-9dd12f67a62b49678877feffc346b9e9
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07834052B2

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