Triethylamine → Boc-Ile-Pro-OBzl

HRID 1073996ノート

反応式

HRID 1073996 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[C@H:10]([CH2:12][CH3:13])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:18]([O:25][C:26](=[O:32])[C@@H:27]1[CH2:31][CH2:30][CH2:29][NH:28]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:18]([O:25][C:26](=[O:32])[C@@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C:14](=[O:16])[C@H:9]([C@H:10]([CH2:12][CH3:13])[CH3:11])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 2733413Proline benzyl ester hydrochloride

生成物 1

HCID 14306235Boc-Ile-Pro-OBzl収率 93.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N-t-butyloxycarbonyl-L-isoleucine 1/2 hydrate 36.05 g, 150 mmole), L-proline benzylester hydrochloride 36.26 g, 150 mmole) and HOBT (20.26 g, 150 mmole) were dissolved in methylene chloride (500 ml), and triethylamine 18 g, 150 mmole) and WSC hydrochloride (28.76 g, 150 mmole) were added thereto at -30° C. The mixture was stirred for 2 hours at less than 0° C. and then overnight at room temperature, and the solution was washed with 5% aqueous sodium bicarbonate (500 ml, twice), 5% aqueous citric acid (500 ml, twice) and water (508 ml) in the order given, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give N-t-butyloxycarbonyl-L-isoleucyl-L-proline benzylester(yield: 58.43 g, 93.1%).

後処理

  1. customat -30° C
  2. washovernight at room temperature, and the solution was washed with 5% aqueous sodium bicarbonate (500 ml
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-a5e9ac34783d4fb99a77858c7ee69f46
出典データセット
uspto-grants-1990_11
特許番号
US04971993

反応ノート

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