Gemcitabine Hydrochloride → HCID 86718328, compound

HRID 1849942Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:3].[CH:12]1[C:18]([NH2:19])=[N:17][C:15](=[O:16])[N:14]([C@@H:20]2[O:24][C@H:23]([CH2:25][OH:26])[C@@H:22]([OH:27])[C:21]2([F:29])[F:28])[CH:13]=1.Cl>>[F:29][C:21]1([F:28])[C@H:22]([OH:27])[C@@H:23]([CH2:25][OH:26])[O:24][C@H:20]1[N:14]1[CH:13]=[CH:12][C:18]([NH:19][C:2]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:3])=[N:17][C:15]1=[O:16]

Participants

Reactant 2

HCID 60749Gemcitabine Hydrochloride

HCID 118547Carbonochloridic acid, heptyl ester

Product 1

HCID 86718328HCID 86718328, compoundYield 93%

Procedure

Using Method A and heptyl chloroformate, gemcitabine hydrochloride was converted to 43 (white solid, 93% yield): 1H NMR (200 MHz, DMSO-d6) δ 10.87 (s, 1H), 8.24-8.28 (d, 1H), 7.12-7.16 (d, 1H), 6.33-6.37 (d, 1H), 6.16-6.24 (t, 1H), 5.31-5.36 (t, 1H), 4.19-4.33 (m, 1H), 4.10-4.17 (t, 2H), 3.63-3.94 (m, 3H), 1.60-1.66 (t, 2H), 1.29-1.31 (t, 8H), 0.86-0.92 (t, 3H).

Sources & evidence

ORD record: ord-bda4e0726b7e4b0faa6ca5b72c2c34b7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08956613B2

Reaction notes

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