Ethyl chloroformate → HCID 15283218, compound

HRID 1849937Notes

Reaction equation

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

Participants

Reactant 2

HCID 10928Ethyl chloroformate

HCID 60749Gemcitabine Hydrochloride

Product 1

HCID 15283218HCID 15283218, compoundYield 64%

Procedure

Using Method A and ethyl chloroformate, gemcitabine hydrochloride was converted to 8 (white solid, 64% yield): 1H NMR (400 MHz, DMSO-d6)δ10.88 (s, 1H), 8.24-8.27 (d, 1H), 7.13-7.16 (d, 1H), 6.34-6.37 (d, 1H), 6.18-6.22 (t, 1H), 5.32-5.36 (t, 1H), 4.17-4.23 (m, 3H), 3.90-3.94 (m, 1H), 3.82-3.86 (m, 1H), 3.65-3.72 (m, 1H), 1.25-1.29 (t, 3H); MS (HR-ESI): m/z 334.0853 [M−H]−.

Sources & evidence

ORD record: ord-08845cda8fab4dcfbc3f6d925bfef7f2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08956613B2

Reaction notes

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