4-Methylmorpholine → HCID 58370136, compound

HRID 1889280Notes

Reaction equation

HRID 1889280 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.Cl.[CH3:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[NH2:20].CN1CCOCC1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C=O)C>[CH3:16][O:17][C:18](=[O:23])[C:19]([NH:20][C:12]([C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[Br:1])=[O:14])([CH3:22])[CH3:21]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 886651-Bromo-2-naphthoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 58370136HCID 58370136, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1.0 g 1-bromo-naphthalene-2-carboxylic acid and 0.61 g 2,2-dimethylglycine methyl ester hydrochloride were suspended in 30 ml of dichloromethane and 10 ml of DMF. 1.31 ml N-methylmorpholine, 0.70 g 1-hydroxybenzotriazole and, finally, 0.99 g 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added and the reaction stirred at room temperature for 14 h. The reaction mixture was chromatographed on silica (ethyl acetate/heptane) without aqueous work-up to give 1.3 g 2-[(1-bromo-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester.

Workup

  1. customThe reaction mixture was chromatographed on silica (ethyl acetate/heptane) without aqueous work-up

Sources & evidence

ORD record
ord-45d0fa0f18504aa6a44c64ab5cdb77c1
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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