Hydrogen Sulfide → t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-thiocarbamoylbenzoyl)ureido]phenyl]propionate

HRID 1900887Notes

Reaction equation

HRID 1900887 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:37])[C:29]2[CH:34]=[CH:33][C:32]([C:35]#[N: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].N1C=CC=CC=1.[SH2:44]>C(N(CC)CC)C>[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:37])[C:29]2[CH:34]=[CH:33][C:32]([C:35](=[S:44])[NH2:36])=[CH:31][CH:30]=2)=[O:26])=[CH:20][CH:19]=1)[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])(=[O:6])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 86749999t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-cyanobenzoyl)ureido]phenyl]propionate

Product 1

HCID 57230791t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-thiocarbamoylbenzoyl)ureido]phenyl]propionate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a similar manner to Example 1, starting material step (b), the product of step (d) (2.32 g), pyridine (88 ml), triethylamine (13 ml) and H2S gas were reacted to give t-butyl (2S)-2-(n-butylsulphonylamino)-3-[4-[3-(4-thiocarbamoylbenzoyl)ureido]phenyl]propionate (2.4 g) as a yellow solid: NMR Spectrum (DMSO-d6) 0.79 (3H, t), 1.22 (2H, m), 1.38 (11H, m), 2.70 (2H, t), 2.79 (1H, m), 2.95 (1H, m), 3.95 (1H, m), 7.27 (2H, d), 7.53 (2H, d), 7.68 (1H, d), 7.96 (2H, d), 8.03 (2H, d), 9.66 (1H, br s), 10.05 (1H, br s), 10.74 (1H, s), 11.10 (1H, s); Mass Spectrum m/Z 563 (M+H)+.

Sources & evidence

ORD record
ord-2373fbc964f9431581faa8f1565571a2
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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