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

HRID 426962노트

반응식

HRID 426962 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-93db830dfaa0488fae758e9a32a52970
출처 데이터셋
uspto-grants-1979_10
특허 번호
US04172130

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