Gemcitabine Hydrochloride → HCID 86718326, compound

HRID 1849938Notes

Reaction equation

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

Participants

Reactant 2

HCID 60749Gemcitabine Hydrochloride

HCID 61140Butyl chloroformate

Product 1

HCID 86718326HCID 86718326, compoundYield 91%

Procedure

Using Method A and butyl chloroformate, gemcitabine hydrochloride was converted to 15 (white solid, 91% yield): 1H NMR (200 MHz, DMSO-d6) δ 10.87 (s, 1H), 8.23-8.27 (d, 1H), 7.11-7.15 (d, 1H), 6.37 (s, 1H), 6.16-6.23 (t, 1H), 5.33 (s, 1H), 4.12-4.18 (t, 2H), 3.65-3.95 (m, 4H), 1.44-1.66 (m, 2H), 1.33-1.40 (m, 2H), 0.93-0.97 (t, 3H).

Sources & evidence

ORD record: ord-501d23c26f3b45588c3393d859d361fa
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08956613B2

Reaction notes

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