Hydrochloric Acid → HCID 66701197, compound

HRID 2075493Notes

Reaction equation

HRID 2075493 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[C:4]([C:24](O)=[O:25])[CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.[CH3:38][O:39][C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[NH2:42].C(N(C(C)C)CC)(C)C.Cl>O.CN(C=O)C.C(Cl)CCl>[CH3:38][O:39][C:40](=[O:45])[C:41]([NH:42][C:24]([C:4]1[CH:3]=[C:2]([F:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=[O:25])([CH3:44])[CH3:43]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 23132783HCID 23132783, compound

Product 1

HCID 66701197HCID 66701197, compoundYield 81.4%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 0.2 g of 4-fluoro-1-[4-(trifluoromethyl)benzyloxy]naphthalene-2-carboxylic acid, 158 mg of EDC, 104 mg of 1-hydroxybenzotriazole and 102 mg of 2,2-dimethylglycine methyl ester hydrochloride was added 5.3 ml of DMF followed by 0.29 ml of diisopropylethylamine. The mixture was stirred for 16 h at room temperature. The mixture was poured into cold water, acidified to pH 2-3 with 1M HCl, extracted with ethyl acetate, washed with water, brine, dried (sodium sulphate) filtered and concentrated to an oil. The material was flash chromatographed on silica gel eluting with ethyl acetate/heptanes to provide 0.207 g of 2-{[4-fluoro-1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried (sodium sulphate)
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customchromatographed on silica gel eluting with ethyl acetate/heptanes

Sources & evidence

ORD record
ord-a15295557e2e4f00975bd93cc315ff3f
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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