Diisopropylethylamine → (S)-2-Amino-N-{2,6-dimethyl-4-[methyl-(4-trifluoromethyl-benzyl)-amino]-phenyl}-3-methyl-butyramide

HRID 1820139Notes

Reaction equation

HRID 1820139 reaction equation
C(OC([NH:8][C@H:9]([C:13](O)=[O:14])[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.C(N(CC)C(C)C)(C)C.[CH3:25][C:26]1[CH:31]=[C:30]([N:32]([CH3:44])[CH2:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=2)[CH:29]=[C:28]([CH3:45])[C:27]=1[NH2:46]>CN(C)C=O.[Cl-].[Na+].O>[NH2:8][C@@H:9]([CH:10]([CH3:12])[CH3:11])[C:13]([NH:46][C:27]1[C:26]([CH3:25])=[CH:31][C:30]([N:32]([CH3:44])[CH2:33][C:34]2[CH:35]=[CH:36][C:37]([C:40]([F:41])([F:42])[F:43])=[CH:38][CH:39]=2)=[CH:29][C:28]=1[CH3:45])=[O:14]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 83693Boc-L-ValineHCID 685154092,6,N'-trimethyl-N'-(4-trifluoromethyl-benzyl)-benzene-1,4-diamine

Product 1

HCID 11567683(S)-2-Amino-N-{2,6-dimethyl-4-[methyl-(4-trifluoromethyl-benzyl)-amino]-phenyl}-3-methyl-butyramide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Tert-butyloxycarbonyl-L-valine (21.7 mg), N,N-diisopropyl-ethylamine (35 uL), N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methyl-methanaminium hexafluoro-phosphate N-oxide (0.38 g) and 2,6,N′-trimethyl-N′-(4-trifluoromethyl-benzyl)-benzene-1,4-diamine (15.4 mg) were mixed in dry N,N-dimethylformamide (0.2 mL) and stirred under argon for 2 hours. Brine (2 mL) was added and the reaction mixture was extracted with ethyl acetate (2×2 mL). The combined organic phases were dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography. 15.4 mg (61% yield) of the N-Boc-protected title compound was isolated and it was dissolved in trifluoroacetic acid/dichloromethane (1:1, 2 mL) and stirred at 25° C. for 30 minutes. The reaction mixture was concentrated in vacuo to furnish 18 mg (96% yield) of the title compound. LC-MS-TOF (m/z) 408 (MH+); tR=2.19, (UV, ELSD) 93%, 98%.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (2×2 mL)
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-22345186d6604d08bced409403378a85
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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