Hexyl chloroformate → HCID 76070824, compound

HRID 1849941Notes

Reaction equation

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

Participants

Reactant 2

HCID 22466Hexyl chloroformate

HCID 60749Gemcitabine Hydrochloride

Product 1

HCID 76070824HCID 76070824, compoundYield 99%

Procedure

Using Method A and hexyl chloroformate, gemcitabine hydrochloride was converted to 36 (white solid, 99% yield): 1H NMR (200 MHz, DMSO-d6) δ 10.88 (s, 1H), 8.23-8.28 (d, 1H), 7.11-7.15 (d, 1H), 6.34-6.37 (d, 1H), 6.16-6.24 (t, 1H), 5.34 (s, 1H), 4.21-4.26 (m, 1H), 4.10-4.18 (t, 2H), 3.65-3.94 (m, 3H), 1.60-1.67 (t, 2H), 1.31-1.33 (t, 6H), 0.87-0.94 (t, 3H).

Sources & evidence

ORD record: ord-64472e2068b7498f90284832b691c77d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08956613B2

Reaction notes

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