Triethylamine → 2-Methylpentane

HRID 516901

Reaction equation

HRID 516901 reaction equation
[Cl:1][C:2]1[C:7]([S:8]([N:11]([O:13][CH3:14])[CH3:12])(=[O:10])=[O:9])=[C:6]([OH:15])[C:5]([NH:16][C:17]2[C:20](=O)[C:19](=[O:22])[C:18]=2[O:23]CC)=[CH:4][CH:3]=1.[CH2:26]([C@@H:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:27].C(N(CC)CC)C>CC#N.CCO.CO.C(Cl)Cl.CCOC(C)=O>[CH3:27][CH2:26][CH2:28][CH:29]([CH3:34])[CH3:30].[Cl:1][C:2]1[C:7]([S:8]([N:11]([O:13][CH3:14])[CH3:12])(=[O:10])=[O:9])=[C:6]([OH:15])[C:5]([NH:16][C:17]2[C:18](=[O:23])[C:19](=[O:22])[C:20]=2[NH:35][C@@H:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:26][CH3:27])=[CH:4][CH:3]=1

Participants

10

Reactant 3

HCID 8471TriethylamineHCID 5324978(R)-1-PhenylpropylamineHCID 568442936-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide2×

Product 2

HCID 78922-MethylpentaneHCID 446289806-Chloro-3-[3,4-dioxo-2-((R)-1-phenyl-propylamino)-cyclobut-1-enylamino]-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of 6-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide (Intermediate A) (100 mg, 0.256 mmol) in MeCN (2 ml) and EtOH (1 ml) under N2 at RT was added (R)-(+)-alpha-ethylbenzylamine (58.8 mg, 0.435 mmol) and triethylamine (0.142 ml, 1.02 mmol) and the reaction mixture was heated at 80° C. overnight. The reaction mixture was concentrated in vacuo to give a yellow solid which was loaded onto a 1 g pre-packed silica column, dissolving in the minimal amount of 5% MeOH in DCM. Purification was carried out eluting with 10-40% EtOAc in iso-hexane and the appropriate fractions were concentrated under vacuum to give a yellow glassy solid. The solid was dissolved in EtOAc and washed four times with 1M HCl (aq). The organic portion was dried (sodium sulfate) and concentrated in vacuo to yield a brown gummy solid. Trituration with iso-hexane afford the title compound as a solid brown solid; [M+H]+ 180. 1H NMR (DMSO) 0.9 (3H, t, CH3), 1.9 (2H, m, CH2), 3.0 (3H, s, CH3), 3.6 (3H, s, CH3), 5.1 (1H, m, CH), 7.2-7.5 (6H, m, Ar—H), 8.0 (1H, d, Ar—H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a yellow solid which
  3. customPurification
  4. washwas carried out eluting with 10-40% EtOAc in iso-hexane
  5. concentrationthe appropriate fractions were concentrated under vacuum
  6. customto give a yellow glassy solid
  7. washwashed four times with 1M HCl (aq)
  8. dry with materialThe organic portion was dried (sodium sulfate)
  9. concentrationconcentrated in vacuo
  10. customto yield a brown gummy solid

Sources & evidence

ORD record
ord-b114f9b55c3941e397cecc5ea87df619
Source dataset
uspto-grants-2015_08
Patent number
US09115087B2

Linked notes

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