Diisopropylethylamine → HCID 12044226, compound

HRID 1976964Notes

Reaction equation

HRID 1976964 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[NH2:6].[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:20]=1[C:21](O)=[O:22].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[NH:6][C:21](=[O:22])[C:20]1[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:19]=1[Cl:18]

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 11715866Methyl 4-nitro-L-phenylalaninate hydrochloride

Product 1

HCID 12044226HCID 12044226, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-nitro-L-phenylalanine methyl ester hydrochloride (1.527 g, 5.86 mmol), 2-chloro-6-methylbenzoic acid (1.0 g, 5.86 mmol) and DIPEA (3.2 mL, 2.3 g, 18 mmol) in DMF (10 mL) was added HBTU (2.22 g, 5.86 mmol) at room temperature. After 4 hr at room temperature, the reaction mixture was diltuted with ethyl acetate (200 mL) and the organic layer was washed with water (20 mL), 1N HCl, NaHCO3 and brine (2×30 mL for each solvent) and dried over NaSO4. After removal of the solvent, the residue was purified by chromatography on silica gel eluting with ethyl acetate:hexane (1:2), to give N-(2-chloro-6-methylbenzoyl)-4-nitro-L-phenyl alanine methyl ester (1.71 g, 4.50 mmol, 77.6%). mp, 123-4° C. Analysis (C18H17ClN2O5) calcd.: C, 57.38, H, 4.55, N, 7.43. Found: C, 57.11, H, 4.58, N, 7.27.

Workup

  1. washthe organic layer was washed with water (20 mL), 1N HCl, NaHCO3 and brine (2×30 mL for each solvent) and
  2. dry with materialdried over NaSO4
  3. customAfter removal of the solvent
  4. customthe residue was purified by chromatography on silica gel eluting with ethyl acetate:hexane (1:2)

Sources & evidence

ORD record
ord-68bcf9198f8e49a6b5593a63808d7b2b
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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