Dimethylformamide → (2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-dimethylaminobenzyl)amino]-4-methylpentanoic acid amide

HRID 1893835Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:20]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]([NH2:23])=[O:22])[CH2:12][C:13]2[CH:18]=[CH:17]C(N)=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.IC.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O.[CH3:42][N:43]([CH:45]=O)[CH3:44]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C@H:20]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]([NH2:23])=[O:22])[CH2:12][C:13]2[CH:14]=[CH:15][C:45]([N:43]([CH3:42])[CH3:44])=[CH:17][CH:18]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

(2R)-2-[N-(4-Chlorobenzene-sulfonyl)-N-(4-aminobenzyl)amino]-4-methyl-pentanoic acid amide (Example 48, 0.10 g, 0.22 mmol) was dissolved in DMF (5 mL). To this solution was added iodomethane (62 mg, 0.44 mmol), and cesium carbonate (220 mg, 0.66 mmol). The reaction was then stirred at 40° C. for 18 h. The reaction was poured into EtOAc and water. The organic was collected, dried over MgSO4, and concentrated to an oily residue. The residue was further purified (BIOTAGE® 40S, loaded in CH2Cl2, eluted in 25% EtOAc/hexanes) to yield a yellow powder (15 mg, 16%). MS (ESI), (M+H)+438.1; 1H NMR (DMSO-d6, 500 MHz) δ 7.74 (dd, 2H, J=1.9, 6.7), 7.54 (dd, 2H, J=1.9, 6.8), 7.43 (s, 1H), 7.16 (d, 2H, J=8.6), 7.01 (s, 1H), 6.61 (d, 2H, J=8.8), 4.59 (q, 2H, J=16, 25), 4.34 (dd, 1H, J=5.0, 9.3), 2.85 (s, 6H), 1.27-1.47 (m, 3H), 0.80 (d, 3H, J=5.9), 0.52 (d, 3H, J=6.1).

Workup

customThe organic was collected
dry with materialdried over MgSO4
concentrationconcentrated to an oily residue
customThe residue was further purified
wash(BIOTAGE® 40S, loaded in CH2Cl2, eluted in 25% EtOAc/hexanes)

Sources & evidence

ORD record: ord-f0d191ce5e9e4915a46875e1888f28f8
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513253B2

Reaction notes

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