Triethylamine → HCID 69290318, compound

HRID 1247249Notes

Reaction equation

Cl.[C:2]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][C:11](=[O:24])[CH:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[F:23])[O:13][CH3:14])=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29].C(N(CC)CC)C.C(OCC)(=O)C>CN(C=O)C>[CH2:31]([O:30][C:28](=[O:29])[N:4]=[C:2]([NH2:3])[C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:11](=[O:24])[CH:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[F:23])[O:13][CH3:14])=[CH:25][CH:26]=1)[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

(RS)-N-(4-Carbamimidoyl-benzyl)-2-(2-fluoro-4-methoxy-phenyl)-2-methoxy-acetamide hydrochloride (example 15.3, 200 mg) was dissolved in DMF (2.2 ml). The flask was placed in an ice bath. Ethyl chloroformate (58 mg) and triethylamine (160 mg) were added dropwise. The reaction mixture was stirred for 1.5 h at 0° C. Ethyl acetate (30 ml) and ice water (40 ml) were added and the mixture was extracted with ethyl acetate. The organic phase was washed with water, dried, filtered and evaporated. The product was purified by chromatography (silicagel, ethylacetate) to give (RS)-[amino-(4-{[2-(2-fluoro-4-methoxy-phenyl)-2-methoxy-acetylamino]-methyl}-phenyl)-methylene]-carbamic acid ethyl ester (218 mg) as a colorless amorphous solid. MS 418.3 ([M+H]+)

Workup

customThe flask was placed in an ice bath
extractionthe mixture was extracted with ethyl acetate
washThe organic phase was washed with water
customdried
filtrationfiltered
customevaporated
customThe product was purified by chromatography (silicagel, ethylacetate)

Sources & evidence

ORD record: ord-f9f34f76beec460581da210d73ebfe95
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129238B2

Reaction notes

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