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

HRID 1746478
ノート
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反応式

HRID 1746478 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ed617820a53c463ebf01671910f6d0f9
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150510B2

反応ノート

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