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

HRID 1893835
Notes
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Reaction equation

HRID 1893835 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 59001017(2R)-2-[(4-aminobenzyl)-(4-chloro-benzenesulfonyl)amino]-4-methyl-pentanoic acid amide

Product 1

HCID 59432818
(2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-dimethylaminobenzyl)amino]-4-methylpentanoic acid amide
Yield 16%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. customThe organic was collected
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to an oily residue
  4. customThe residue was further purified
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes