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Diisopropylethylamine → N-[[1-(2-azidoethyl)cyclopentyl]carbonyl]-4nitro-L-phenylalanine methyl ester

HRID 1018134
ノート
印刷プレビュー

反応式

HRID 1018134 の反応式
Cl.[CH3:2][O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[NH2:6].[N:18]([CH2:21][CH2:22][C:23]1([C:28](O)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]1)=[N+:19]=[N-:20].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCl.CN(C=O)C.O.C(OCC)(=O)C.CCCCCC>[CH3:2][O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[NH:6][C:28]([C:23]1([CH2:22][CH2:21][N:18]=[N+:19]=[N-:20])[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11715866Methyl 4-nitro-L-phenylalaninate hydrochlorideHCID 226601251-(2-Azidoethyl)cyclopentanecarboxylic acid

生成物 1

HCID 12042583N-[[1-(2-azidoethyl)cyclopentyl]carbonyl]-4nitro-L-phenylalanine methyl ester収率 95.1%

試薬・触媒・溶媒 5

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4-nitro-L-phenylalanine methyl ester hydrochloride (3.0 g, 11.5 mmol), 1-(2-azidoethyl)cyclopentane carboxylic acid (2.3 g, 12.7 mmol) and BOP (5.34 g, 12.1 mmol) in dichloromethane (6 mL) and DMF (4 mL) was treated with diisopropylethylamine (4.2 mL, 24.2 mmol). The mixture was stirred overnight at which time TLC (1:1 hexane:ethyl acetate) indicated no more starting material. The mixture was diluted with water, extracted with ethyl acetate. The extracts were washed with water and brine, then were dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by chromatography over silica gel (3:1 hexane:ethyl acetate) to afford 4.26 g of N-[[1-(2-azidoethyl)cyclopentyl]carbonyl]-4-nitro-L-phenylalanine methyl ester.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water and brine
  3. dry with materialwere dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography over silica gel (3:1 hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-31b220c790b040cc9630e34cbc648af3
出典データセット
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06479666B2

反応ノート

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