Gemcitabine Hydrochloride → HCID 86718327, compound

HRID 1849939Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[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][CH:6]([CH3:8])[CH3:7])=[O:3])=[N:14][C:12]1=[O:13]

Participants

Reactant 2

HCID 60749Gemcitabine Hydrochloride

HCID 62365Isobutyl chloroformate

Product 1

HCID 86718327HCID 86718327, compoundYield 97%

Procedure

Using Method A and isobutyl chloroformate, gemcitabine hydrochloride was converted to 22 (white solid, 97% yield): 1H NMR (500 MHz, DMSO-d6) δ 10.88 (s, 1H), 8.25-8.26 (d, 1H), 7.12-7.14 (d, 1H), 6.35 (s, 1H), 6.19-6.22 (t, 1H), 5.33 (s, 1H), 4.22-4.24 (d, 1H), 3.91-3.96 (m, 3H), 3.83-3.85 (d, 1H), 3.68-3.70 (d, 1H), 1.91-1.97 (m, 1H), 0.94-0.95 (d, 6H).

Sources & evidence

ORD record: ord-153f951c5dbd4794ab2bc00b80ef9ca5
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08956613B2

Reaction notes

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