Triethylamine → (2R)-N-benzyl-N-benzyloxycarbonylmethyl-2-(tert-butoxycarbonylamino)-3-(N-formyl-1H-indol-3-yl)propanamide

HRID 1379180ノート

反応式

HRID 1379180 の反応式
N#N.[C:3]([O:7][C:8]([NH:10][C@@H:11]([C:24](O)=[O:25])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH:22]=[O:23])[CH:14]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl.[CH2:28]([O:35][C:36](=[O:46])[CH2:37][NH:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>ClCCl.O>[CH2:39]([N:38]([CH2:37][C:36]([O:35][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:46])[C:24](=[O:25])[C@H:11]([NH:10][C:8]([O:7][C:3]([CH3:5])([CH3:6])[CH3:4])=[O:9])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH:22]=[O:23])[CH:14]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 21616628N-benzylglycine benzyl ester hydrochlorideHCID 86751286N2 (tert-butoxycarbonyl)-N1-formyl-D-tryptophan

生成物 1

HCID 54067756(2R)-N-benzyl-N-benzyloxycarbonylmethyl-2-(tert-butoxycarbonylamino)-3-(N-formyl-1H-indol-3-yl)propanamide収率 101.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of N2 -(tert-butoxycarbonyl)-N1 -formyl-D-tryptophan (3.99 g) and N-benzyl glycin benzyl ester hydrochloride (3.50 g) in dichloromethane (70 ml) was added triethylamine (5.85 ml) under nitrogen atmosphere. To the mixture was added 2-chloro-1-methylpyridinium iodide (3.67 g) at room temperature, and the resulting mixture was stirred for 2 hours. After the reaction was completed, dichloromethane (30 ml) and water (30 ml) were added. The organic layer was separated, washed with 0.5N hydrochloric acid (10 ml), water (10 ml), aqueous sodium bicarbonate solution (10 ml) and brine (20 ml) successively and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified on a silica gel column (140 g) eluting with a mixture of toluene and ethyl acetate (4:1) to give (2R)-N-benzyl-N-benzyloxycarbonylmethyl-2-(tert-butoxycarbonylamino)-3-(N-formyl-1H-indol-3-yl)propanamide (6.41 g) as an oil.

後処理

  1. customThe organic layer was separated
  2. washwashed with 0.5N hydrochloric acid (10 ml), water (10 ml), aqueous sodium bicarbonate solution (10 ml) and brine (20 ml) successively
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was purified on a silica gel column (140 g)
  6. washeluting with a mixture of toluene and ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-3210084c292d49afa3c7fb096263aac5
出典データセット
uspto-grants-1997_09
特許番号
US05670505

反応ノート

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