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Methyl isothiocyanate → N-[2-chloro-4-(3-methylthioureido)benzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

HRID 24654
Notes
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Reaction equation

HRID 24654 reaction equation
[CH3:1][N:2]=[C:3]=[S:4].[CH3:5][O:6][C:7](=[O:35])[C@H:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])=[CH:23][CH:22]=1)[NH:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=1[Cl:18].CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH3:5][O:6][C:7](=[O:35])[C@H:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])=[CH:23][CH:22]=1)[NH:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:3]([NH:2][CH3:1])=[S:4])=[CH:13][C:12]=1[Cl:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11167Methyl isothiocyanateHCID 81531DiisopropylethylamineHCID 54392214N-(4-amino-2-chlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

Product 1

HCID 54405488N-[2-chloro-4-(3-methylthioureido)benzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

Reagents, catalysts & solvents 3

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Methylisothiocyanate (43 μL) was added to a solution of N-(4-amino-2-chlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (55.1 mg) in anhydrous DMF (1 mL) containing DIEA (22 μL) and DMAP (catalitic amount). The resulting mixture was then heated at 90° C. under N2 for 1 d. After cooling, the mixture was diluted with EtOAc, washed sequentially with 1N HCl, satd. NaHCO3 and water, dried (MgSO4) and evaporated. The residue was purified by preparative TLC (silica gel) using CH2Cl2/MeOH (15:1) as an eluent to give N-[2-chloro-4-(3-methylthioureido)benzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (22.7 mg). ESMS: m/z 512 (MH+).

Workup

  1. temperatureAfter cooling
  2. washwashed sequentially with 1N HCl
  3. dry with materialNaHCO3 and water, dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by preparative TLC (silica gel)

Sources & evidence

ORD record
ord-258276ba663a44b99a5259d13e255860
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855843B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes