Hydrogen Sulfide → HCID 23370006, compound

HRID 1900910Notes

Reaction equation

HRID 1900910 reaction equation
[C:1]([C:3]1[CH:34]=[CH:33][C:6]([C:7]([NH:9][C:10](=[O:32])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([CH2:27][CH2:28][O:29][CH2:30][CH3:31])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:14][CH:13]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2].N1C=CC=CC=1.[SH2:41]>C(N(CC)CC)C>[CH2:30]([O:29][CH2:28][CH2:27][CH:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([C:1](=[S:41])[NH2:2])=[CH:34][CH:33]=2)=[O:32])=[CH:13][CH:14]=1)[C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH3:31]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 23370038HCID 23370038, compound

Product 1

HCID 23370006HCID 23370006, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a similar manner to Example 1, starting material step (b), the product of step (e) (600 mg), pyridine (42 ml), triethylamine (6 ml) and H2S gas were reacted to give t-butyl 2-(2-ethoxyethyl)-3-(4-[3-(4-thiocarbamoylbenzoyl)ureido]phenyl)propionate (585 mg) as a yellow solid: m.p. 199°-201° C.; NMR Spectrum (DMSO-d6) 1.10 (3H, t), 1.30 (9H, s), 1.70 (2H, m), 2.62 (1H, m), 2.72 (2H, m), 3.37 (4H, m), 7.15 (2H, d), 7.49 (2H, d), 7.95 (2H, d), 8.03 (2H, d), 9.67 (1H, br s), 10.06 (1H, br s), 10.72 (1H, s), 11.09 (1H, s); Mass Spectrum m/Z 522 (M+H)+.

Sources & evidence

ORD record
ord-20a04ff0ff924ea5805cb712f66b0f7b
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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