2,6-Lutidine → S-(2-Aminophenyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine, methyl ester

HRID 1981141Notes

Reaction equation

HRID 1981141 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].N1C(C)=CC=CC=1C.[CH3:17][C:18]([CH3:30])([O:20][C:21]([NH:23][C:24](=[CH2:29])[C:25]([O:27][CH3:28])=[O:26])=[O:22])[CH3:19]>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:29][C@@H:24]([C:25]([O:27][CH3:28])=[O:26])[NH:23][C:21]([O:20][C:18]([CH3:30])([CH3:17])[CH3:19])=[O:22]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 87132-AminothiophenolHCID 10932500Methyl 2-((tert-butoxycarbonyl)amino)prop-2-enoate

Product 1

HCID 131713585S-(2-Aminophenyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine, methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-amino-thiophenol (1.9 g., 15.4 mmole), methylene chloride (15 ml.), and 2,6-lutidine (1.8 ml., 1.0 eq.) at -20° (chloroform dry ice) is added 2-[[(1,1-dimethylethoxy)carbonyl]amino]-2-propenoic acid, methyl ester (3.0 g., 1.0 eq.) dropwise over 5 minutes. After one hour the cooling bath is removed and the reaction mixture is stirred for an additional 16 hours. The reaction mixture is diluted with ethyl acetate and washed with saturated sodium bicarbonate, water, brine, dried (MgSO4), and evaporated. The residue (4.1 g.) is chromatographed on silica (125 g.) eluting with hexane/ethyl acetate (5:1) to give 2.5 g. of S-(2-aminophenyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine, methyl ester as an oil after evaporation.

Workup

  1. customAfter one hour the cooling bath is removed
  2. additionThe reaction mixture is diluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate, water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue (4.1 g.) is chromatographed on silica (125 g.)
  7. washeluting with hexane/ethyl acetate (5:1)
  8. customto give 2.5 g
  9. customof S-(2-aminophenyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine, methyl ester as an oil after evaporation

Sources & evidence

ORD record
ord-01309ff9460f443a945cb17665019e0c
Source dataset
uspto-grants-1985_04
Patent number
US04512988

Reaction notes

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