Gemcitabine Hydrochloride → HCID 86718329, compound

HRID 1849943Notes

Reaction equation

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

Participants

Reactant 2

HCID 60749Gemcitabine Hydrochloride

HCID 694002-Methoxyethyl chloroformate

Product 1

HCID 86718329HCID 86718329, compoundYield 60%

Procedure

Using Method A and 2-methoxyethyl chloroformate, gemcitabine hydrochloride was converted to 50 (white solid, 60% yield): 1H NMR (500 MHz, DMSO-d6) δ 10.92 (s, 1H), 8.25-8.27 (d, 1H), 7.11-7.13 (d, 1H), 6.30-6.32 (t, 1H), 6.18-6.22 (t, 1H), 5.32-5.35 (t, 1H), 4.23-4.26 (m, 2H), 4.13-4.22 (m, 1H), 3.86-3.90 (m, 1H), 3.78-3.81 (m, 1H), 3.62-3.66 (m, 1H), 3.54-3.57 (m, 2H), 3.32 (s, 3H).

Sources & evidence

ORD record: ord-ffa76cec24f948ec9613c3567c5c2334
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08956613B2

Reaction notes

Loading…