Diisopropylethylamine → HCID 15908953, compound

HRID 844840Notes

Reaction equation

HRID 844840 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:24])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15](=[O:23])[N:16]([CH3:22])[C:17](=[O:21])[N:18]([CH3:20])[CH:19]=2)=[CH:10][CH:9]=1)[NH2:6].[Cl:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:27]=1[C:28](O)=[O:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:24])[C@H:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15](=[O:23])[N:16]([CH3:22])[C:17](=[O:21])[N:18]([CH3:20])[CH:19]=2)=[CH:12][CH:13]=1)[NH:6][C:28]([C:27]1[C:31]([CH3:35])=[CH:32][CH:33]=[CH:34][C:26]=1[Cl:25])=[O:29]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 888702-Chloro-6-methylbenzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69337884HCID 69337884, compound

Product 1

HCID 15908953HCID 15908953, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension 4-(1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester hydrochloride salt (0.5 mmol, 0.180 g), 2-chloro-6-methylbenzoic acid (0.55 mmol, 0.084 g) and HBTU (0.6 mmol, 0.227 g) in DMF (4 mL) was added diisopropylethylamine (3.0 mmol, 0.52 mL) at room temperature. After 1 min, everything went into solution and the yellow clear solution was stirred 15 h at room temperature. By this time, it turned to a brown solution was diluted with ethyl acetate (25 mL). The ethyl acetate layer was washed successively with water (2×20 mL), saturated sodium bicarbonate solution (25 mL), and brine solution (25 mL) and was dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent gave the crude product which was purified by silica gel column chromatography to afford 151.5 mg (72% yield) of N-[(2-chloro-6-methylphenyl)carbonyl]-4-(1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine methyl ester as a white solid: mp 155-157° C. EI-HRMS m/e calcd for C24H24N3O5Cl (M+) 470.1483, found 470.1484.

Workup

  1. washThe ethyl acetate layer was washed successively with water (2×20 mL), saturated sodium bicarbonate solution (25 mL), and brine solution (25 mL)
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. filtrationFiltration of the drying agent and concentration of the solvent
  4. customgave the crude product which
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ce24066f82954b76b982c87a9c582f29
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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