Ethyl Acetate → (Z)-2-benzyloxycarbonylamino-3-(6-methoxy-[1,5]naphthyridin-4-yl)-acrylic acid methyl ester

HRID 1640513Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[CH:4]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])P(OC)(OC)=O.C1CCN2C(=NCCC2)CC1.[CH3:34][O:35][C:36]1[N:37]=[C:38]2[C:43](=[CH:44][CH:45]=1)[N:42]=[CH:41][CH:40]=[C:39]2[CH:46]=O.CC(=O)OCC>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])/[C:4](/[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])=[CH:46]/[C:39]1[C:38]2[C:43](=[CH:44][CH:45]=[C:36]([O:35][CH3:34])[N:37]=2)[N:42]=[CH:41][CH:40]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of benzyloxycarbonylamino-(dimethoxy-phosphoryl)-acetic acid methyl ester (2.07 g, 6.25 mmol) in DCM (10 mL) was cooled to 0° C. and DBU (0.95 g, 6.25 mmol) was added dropwise. The mixture was stirred at 0° C. for 15 min and then added via syringe dropwise to a suspension of 6-methoxy-[1,5]naphthyridine-4-carbaldehyde (0.94 g, 5 mmol) in DCM (15 mL) at 0° C. The mixture was stirred at 0° C. for 1 h, diluted with DCM, washed with water, dried over MgSO4 and concentrated. Chromatography on SiO2 (Hex/EA 1:1) gave the product (25:1 Z/E mixture) as a colourless foam (1.92 g, 98% yield).

Workup

stirringThe mixture was stirred at 0° C. for 1 h
washwashed with water
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-99ed22d618cf4435bf6a00d3e47bc208
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114867B2

Reaction notes

Loading…