Thiourea → HCID 178462293, compound

HRID 1840463Notes

Reaction equation

Br[CH2:2][CH2:3][S:4][C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[C:11]([C:13]3[C@H:14]([CH3:37])[C@@H:15]4[C@@H:32]([C@H:33]([OH:35])[CH3:34])[C:31](=[O:36])[N:16]4[C:17]=3[C:18]([O:20]CC3C=CC([N+]([O-])=O)=CC=3)=[O:19])[S:10][C:9]=12.[NH2:38][C:39]([NH2:41])=[S:40]>C(#N)C.CN(C=O)C>[OH:35][C@@H:33]([C@H:32]1[C:31](=[O:36])[N:16]2[C:17]([C:18]([OH:20])=[O:19])=[C:13]([C:11]3[S:10][C:9]4=[C:5]([S:4][CH2:3][CH2:2][NH:41][C:39](=[NH:38])[SH:40])[N:6]=[CH:7][N:8]4[CH:12]=3)[C@H:14]([CH3:37])[C@H:15]12)[CH3:34]

Participants

Conditions

Temperature: 50 °C

Procedure

4-Nitrobenzyl (1S,5R,6S)-2-[7-(2-bromoethyl)thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (128 mg) was dissolved in 3 ml of acetonitrile and 0.5 ml of DMF. Thiourea (222 mg) was added to the solution. The mixture was stirred at 50° C. for 18 hr. The reaction solution was concentrated under the reduced pressure. The residue was purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1), followed by a reaction and purification in the same manner as in Example 1c). Thus, 14.5 mg of the title compound was prepared.

Workup

concentrationThe reaction solution was concentrated under the reduced pressure
customThe residue was purified by column chromatography on Sephadex
custom(dichloromethane:methanol=1:1), followed by a reaction and purification in the same manner as in Example 1c)

Sources & evidence

ORD record: ord-3483269283174fa69e6c47756df22efb
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680313B2

Reaction notes

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