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

HRID 841157Notes

Reaction equation

HRID 841157 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9fdc2b11c24a4b71b79e4d1db6c45c10
Source dataset
uspto-grants-2002_04
Patent number
US06369272B1

Reaction notes

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