Triethylamine → 6-Chloro-2-hydroxy-N-methoxy-3-[2-((R)-1-methoxymethyl-2-methyl-propylamino)-3,4-dioxo-cyclobut-1-enylamino]-N-methyl-benzenesulfonamide

HRID 516906

Reaction equation

[CH2:1](N(CC)CC)C.[NH2:8][C@H:9]([CH:12]([CH3:14])[CH3:13])[CH2:10][OH:11].[Cl:15][C:16]1[C:21]([S:22]([N:25]([O:27][CH3:28])[CH3:26])(=[O:24])=[O:23])=[C:20]([OH:29])[C:19]([NH:30][C:31]2[C:34](=O)[C:33](=[O:36])[C:32]=2[O:37]CC)=[CH:18][CH:17]=1>CCO>[Cl:15][C:16]1[C:21]([S:22]([N:25]([O:27][CH3:28])[CH3:26])(=[O:23])=[O:24])=[C:20]([OH:29])[C:19]([NH:30][C:31]2[C:32](=[O:37])[C:33](=[O:36])[C:34]=2[NH:8][C@@H:9]([CH2:10][O:11][CH3:1])[CH:12]([CH3:14])[CH3:13])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of triethylamine (1.192 ml, 8.55 mmol) and (R)-2-Amino-3-methyl-butan-1-ol (Intermediate H) in EtOH (36 ml) was added 6-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide (Intermediate A) (1.67 g, 4.27 mmol). The reaction mixture was heated at 85° C. for 18 hours. The reaction mixture was concentrated in vacuo and dissolved in EtOAc. The EtOAc solution was washed with 1M HCl(aq) and NaHCO3 (aq). The NaHCO3 (aq) layer was extracted with EtOAc. The EtOAc layers were combined and concentrated in vacuo. The residue was purified using flash chromatography (0-10% MeOH in DCM) to furnish a brown solid [M+H]+ 462.0.

Workup

concentrationThe reaction mixture was concentrated in vacuo
dissolutiondissolved in EtOAc
washThe EtOAc solution was washed with 1M HCl(aq) and NaHCO3 (aq)
extractionThe NaHCO3 (aq) layer was extracted with EtOAc
concentrationconcentrated in vacuo
customThe residue was purified
customto furnish a brown solid [M+H]+ 462.0

Sources & evidence

ORD record: ord-a0d44ceef7004143a68b7e6c54feefb1
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115087B2

Linked notes

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