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Triethylamine → Methyl Nalpha-[3-(2-Acetoxyphenyl)acryloyl]-L-Tryptophanate

HRID 1746478
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HRID 1746478 반응식
C(N(CC)CC)C.[C:8]([O:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1[CH:14]=[CH:15][C:16]([OH:18])=O)(=[O:10])[CH3:9].CCN=C=NCCCN(C)C.Cl.Cl.[NH2:36][C@H:37]([C:48]([O:50][CH3:51])=[O:49])[CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[NH:41][CH:40]=1>C(Cl)Cl>[C:8]([O:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1[CH:14]=[CH:15][C:16]([NH:36][C@H:37]([C:48]([O:50][CH3:51])=[O:49])[CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[NH:41][CH:40]=1)=[O:18])(=[O:10])[CH3:9]
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 414863-(2-Acetoxyphenyl)-2-propenoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734891Methyl tryptophanate hydrochloride

생성물 1

HCID 86655437Methyl Nalpha-[3-(2-Acetoxyphenyl)acryloyl]-L-Tryptophanate수율 76.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (4.8 mL), 2-acetoxycinnamic acid (7.1 g) and WSC.HCl (6.6 g) were added to a methylene chloride (180 mL) suspension of methyl L-tryptophanate hydrochloride (7.3 g) at 0° C. The mixture was stirred for 20 hours at room temperature. The reaction mixture was washed with water, and thereafter the organic layer was dried over anhydrous sodium sulfate. The residual oily product obtained by distilling off the solvent under a reduced pressure was purified by silica gel column chromatography (BW-127ZH, chloroform:methanol=100:1), to give the captioned compound (8.9 g, 76%) as crystals.

후처리

  1. washThe reaction mixture was washed with water
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customThe residual oily product obtained
  4. distillationby distilling off the solvent under a reduced pressure
  5. customwas purified by silica gel column chromatography (BW-127ZH, chloroform:methanol=100:1)

출처 및 근거

ORD 기록
ord-ed617820a53c463ebf01671910f6d0f9
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150510B2

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