Veratrylamine → HCID 118217189, compound

HRID 1507196Notes

Reaction equation

HRID 1507196 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][NH2:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:13]([O:17][C:18]([NH:20][C@H:21]([CH2:25][CH2:26][S:27][CH3:28])[C:22](O)=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:13]([O:17][C:18](=[O:19])[NH:20][C@H:21]([CH2:25][CH2:26][S:27][CH3:28])[C:22]([NH:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:23])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 79832VeratrylamineHCID 81531DiisopropylethylamineHCID 111051N-(tert-Butyloxycarbonyl)-D-methionineHCID 2724699PyBOP

Product 1

HCID 118217189HCID 118217189, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of (3,4-dimethoxyphenyl)methanamine (2 g, 12 mmol) in DCM (20 mL) was added sequentially (R)-2-((tert-butoxycarbonyl)amino)-4-(methylthio)butanoic acid (3.28 g, 13.2 mmol), PyBOP (6.85 g, 13.2 mmol) and DIPEA (4.18 mL, 23.92 mmol). The reaction mixture was stirred and allowed to warm up to ambient temperature over 2 h. The reaction was then quenched by the addition of water and the mixture was extracted twice with 100 mL DCM. The organic fraction was washed with 50 mL water, 50 mL brine, and the layers were separated. The organic fraction was dried over sodium sulfate, filtered, and evaporated. The residue was purified via silica gel chromatography, eluting with 30% ethyl acetate/petroleum ether. Yield 3.5 gms (R)-tert-butyl(1-((3,4-dimethoxybenzyl)amino)-4-(methylthio)-1-oxobutan-2-yl)carbamate. LCMS (Method F) RT 2.3 min, m/z 399.2 (MH+); 1H NMR (400 MHz, chloroform-d) δ 1.41 (s, 9H), 1.91-1.98 (m, 1H), 2.07 (s, 3H), 2.10-2.14 (m, 1H), 2.47-2.61 (m, 2H), 3.65 (s, 6H), 4.25-4.27 (br s, 1H), 4.33-4.42 (m, 2H), 5.16 (br s, 1H), 6.47 (br s, 1H), 6.80 (s, 3H).

Workup

  1. customThe reaction was then quenched by the addition of water
  2. extractionthe mixture was extracted twice with 100 mL DCM
  3. washThe organic fraction was washed with 50 mL water, 50 mL brine
  4. customthe layers were separated
  5. dry with materialThe organic fraction was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified via silica gel chromatography
  9. washeluting with 30% ethyl acetate/petroleum ether
  10. customLCMS (Method F) RT 2.3 min, m/z 399.2 (MH+)

Sources & evidence

ORD record
ord-6d07ffa9b6084a24ba35feef61b930c6
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

Loading…