Gemcitabine Hydrochloride → HCID 58957814, compound

HRID 1849940Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:3].[CH:10]1[C:16]([NH2:17])=[N:15][C:13](=[O:14])[N:12]([C@@H:18]2[O:22][C@H:21]([CH2:23][OH:24])[C@@H:20]([OH:25])[C:19]2([F:27])[F:26])[CH:11]=1.Cl>>[F:27][C:19]1([F:26])[C@H:20]([OH:25])[C@@H:21]([CH2:23][OH:24])[O:22][C@H:18]1[N:12]1[CH:11]=[CH:10][C:16]([NH:17][C:2]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:3])=[N:15][C:13]1=[O:14]

Participants

Reactant 2

HCID 60749Gemcitabine Hydrochloride

HCID 69489Pentyl chloroformate

Product 1

HCID 58957814HCID 58957814, compoundYield 95%

Procedure

Using Method A and pentyl chloroformate, gemcitabine hydrochloride was converted to 29 (white solid, 95% yield): 1H NMR (200 MHz, DMSO-d6) δ 10.87 (s, 1H), 8.23-8.27 (d, 1H), 7.11-7.15 (d, 1H), 6.34-6.37 (d, 1H), 6.16-6.24 (t, 1H), 5.34 (s, 1H), 4.11-4.18 (t, 3H), 3.82-3.94 (m, 2H), 3.57-3.72 (m, 1H), 1.61-1.68 (t, 2H), 1.34-1.38 (t, 4H), 0.88-0.95 (t, 3H).

Sources & evidence

ORD record: ord-c9e7934b86cc4cd082fa1438463ce76a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08956613B2

Reaction notes

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