Acetone → t-Butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-amidinobenzoyl)ureido]phenyl]propionate, acetate salt

HRID 1900882Notes

Reaction equation

HRID 1900882 reaction equation
[CH2:1]([S:5]([NH:8][C@@H:9]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28](=[O:38])[C:29]2[CH:34]=[CH:33][C:32]([C:35](=S)[NH2:36])=[CH:31][CH:30]=2)=[O:26])=[CH:20][CH:19]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].IC.CC(C)=O.C([O-])(=O)C.[NH4+:49]>ClCCl.CO>[C:10]([OH:12])(=[O:11])[CH3:9].[CH2:1]([S:5]([NH:8][C@@H:9]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28](=[O:38])[C:29]2[CH:30]=[CH:31][C:32]([C:35](=[NH:36])[NH2:49])=[CH:33][CH:34]=2)=[O:26])=[CH:20][CH:19]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(=[O:6])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 57230791t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-thiocarbamoylbenzoyl)ureido]phenyl]propionate

Product 1

HCID 131719650t-Butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-amidinobenzoyl)ureido]phenyl]propionate, acetate saltYield 104.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 1, t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-thiocarbamoylbenzoyl)ureido]phenyl]propionate (2.4 g) was reacted with iodomethane (20 ml) and acetone (150 ml) and the resultant product was treated with ammonium acetate (4.4 g), methanol (50 ml) and dichloromethane (50 ml) at ambient temperature. This yielded a crude pale yellow solid (2.3 g), which was crystallised from hot isopropanol to give the title compound (1.35 g) as an off-white solid: NMR Spectrum (DMSO-d6) 0.81 (3H, t), 1.06 (1.2H, d), 1.24 (2H, m), 1.39 (11H, m), 1.78 (3H, s), 2.71 (2H, m), 2.82 (1H, m), 2.98 (1H, m), 3.81 (0.2H, m), 3.99 (1H, m), 7.18 (2H, d), 7.54 (2H, d), 7.94 (2H, d), 8.15 (2H, d), 8.50-10.50 (2H, br), 10.87 (1H, br s); Mass Spectrum m/Z 546 (M+H)+ ; Elemental Analysis: calculated for C26H35N5O6S. 1.0 CH3CO2H. 0.5 H2O 0.2 (CH3)2CHOH: C, 54.8%; H, 6.69%; N, 11.2%; found: C, 54.8%; H, 6.8%; N, 11.0%.

Workup

  1. customThis yielded a crude pale yellow solid (2.3 g), which
  2. customwas crystallised from hot isopropanol

Sources & evidence

ORD record
ord-02932d6fdd684f0894143ce6da8eda8c
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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