Triethylamine → 2-(N-(tert.-Butoxycarbonyl)-L-phenylalanyl-aminooxy)-acetic acid

HRID 426962ノート

反応式

HRID 426962 の反応式
Br.[NH2:2][O:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:8][C:9]([O:12][C:13]([NH:15][C@H:16]([C:24](ON1C(=O)CCC1=O)=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])([CH3:11])[CH3:10].C(N(CC)CC)C>CN(C=O)C.C(O)C>[C:9]([O:12][C:13]([NH:15][C@H:16]([C:24]([NH:2][O:3][CH2:4][C:5]([OH:7])=[O:6])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])([CH3:10])([CH3:11])[CH3:8]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 107447tert-butyl (S)-(1-benzyl-2-((2,5-dioxo-1-pyrrolidinyl)oxy)-2-oxoethyl)carbamateHCID 85822048Aminooxy-acetic acid hydrobromide

生成物 1

HCID 228088902-(N-(tert.-Butoxycarbonyl)-L-phenylalanyl-aminooxy)-acetic acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

6.97 g (40.5 mmoles) of aminooxy-acetic acid hydrobromide are reacted with 14.68 g (40.5 mmoles) of BOC--Phe--OSu in 100 ml of DMF in the presence of 6.3 ml (45 mmoles) of triethylamine. Next day the reaction mixture is evaporated in vacuo, the oily residue is dissolved in 100 ml of chloroform, and the chloroform solution is washed thrice with 1 n hydrochloric acid. The organic solution is dried, evaporated in vacuo, and the oily residue is solidified with diisopropyl ether. The crude product is purified by precipitation from an ethyl acetate-diisopropyl ether solvent system. 9.70 g (74%) of BOC--Phe--OGly--OH are obtained; m.p.: 136°-137° C., Rf5 : 0.4, [α]D : -17.8° (c: 1.0, in ethanol).

後処理

  1. customNext day the reaction mixture is evaporated in vacuo
  2. dissolutionthe oily residue is dissolved in 100 ml of chloroform
  3. washthe chloroform solution is washed thrice with 1 n hydrochloric acid
  4. customThe organic solution is dried
  5. customevaporated in vacuo
  6. customThe crude product is purified by precipitation from an ethyl acetate-diisopropyl ether solvent system
  7. custom9.70 g (74%) of BOC--Phe--OGly--OH are obtained

出典と根拠

ORDレコード
ord-93db830dfaa0488fae758e9a32a52970
出典データセット
uspto-grants-1979_10
特許番号
US04172130

反応ノート

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