1,8-Diazabicyclo(5.4.0)undec-7-ene → (S)-[2-(1-iminoethylamino)ethyl]-L-homocysteine

HRID 841157노트

반응식

HRID 841157 반응식
C([O:5][C:6](=[O:18])[C@H:7]([CH2:16]S)[NH:8][C:9](OC(C)(C)C)=O)(C)(C)C.[S:19](OCCNC(OCC1C=CC=CC=1)=O)([C:22]1C=CC(C)=CC=1)(=O)=O.[N:43]12CCC[N:50]=[C:49]1[CH2:48]CCC[CH2:44]2>C1(C)C=CC=CC=1>[NH:50]=[C:49]([NH:43][CH2:44][CH2:9][NH:8][C@H:7]([C:6]([OH:5])=[O:18])[CH2:16][CH2:22][SH:19])[CH3:48]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10468754Boc-L-cysteine tert-Butyl EsterHCID 104979822-(Benzyloxycarbonylamino)ethyl 4-methylbenzenesulfonate

생성물 1

HCID 178465611(S)-[2-(1-iminoethylamino)ethyl]-L-homocysteine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of N-t-butoxycarbonyl cysteine t-butyl ester (prepared by reduction of N-t-butoxycarbonyl cystine t-butyl ester with dithiothreitol) (291 mg, 1 mmol) in dry toluene (20 ml) is added N-benzyloxycarbonyl ethanolamine tosylate (349 mg, 1 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (150 μL, 1 mmol) and the mixture stirred vigorously overnight at room temperature under nitrogen. The mixture is partitioned between 50 ml each of ethyl acetate and 1N aqueous HCl. A further organic extract is combined and these extracts washed with aqueous sodium bicarbonate, water and brine, then dried and evaporated. Purification by column chromatography affords the title compound.

후처리

  1. customThe mixture is partitioned between 50 ml each of ethyl acetate and 1N aqueous HCl
  2. extractionA further organic extract
  3. washthese extracts washed with aqueous sodium bicarbonate, water and brine
  4. customdried
  5. customevaporated
  6. customPurification by column chromatography

출처 및 근거

ORD 기록
ord-9fdc2b11c24a4b71b79e4d1db6c45c10
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369272B1

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