Methanol → HCID 86741745, compound

HRID 1789328Notes

Reaction equation

[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[CH2:17](N(CC)CC)C.CO.C([O:29][CH2:30][CH3:31])(=O)C>>[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@:3]([CH:17]=[CH:31][CH:30]=[O:29])([OH:4])[CH2:2]1

Participants

Reactant 4

HCID 887Methanol

HCID 8471Triethylamine

HCID 8857Ethyl Acetate

HCID 13712Deoxyuridine

Product 1

HCID 86741745HCID 86741745, compoundYield 34%

Procedure

The procedure used in Example IV is followed utilizing 2'-deoxyuridine (456 mg; 2 mmole) triethylamine (280 μl; 2 mmole) and propargyl aldehyde (200 μl; 4 mmole) to obtain, after preparative TLC (eluant 5% methanol in ethyl acetate), the desired title compound as a pale yellow oil (190 mg; 34% yield) pure by TLC analysis. 1HNMR (DMSO) 5.88 (d, J=8.2 Hz, 1H, N--CH=CH--CO) 6.15 (t,J=6.1 Hz, 1H, N--CH--(O)), 7.04 (q, J1 =8.2 Hz, J2 =14.8 Hz, 1H, --CH=CH--CHO) 8.05 (d,J=8.2 Hz, 1H, N--CH=CH--CO) 8.15 (d,J=14.8, 1H, CH=CH--CHO) 9.60 (d,J=7.8 Hz, 1H, CHO). Mass spectrum m/z (intensity, % base peak), ion: 282 (0.1)M+, 253 (0- 1) (M-CHO)+, 137 (40) 117 (78) 73 (100).

Workup

customto obtain

Sources & evidence

ORD record: ord-151fb1f329b940ba95ba25455a784d4b
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04689321

Reaction notes

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