Methanol → HCID 11567942, compound

HRID 2421823Notes

Reaction equation

HRID 2421823 reaction equation
[OH:1][C@@H:2]1[C@H:7]([OH:8])[C@@H:6]([O:9][CH3:10])[C:5]([CH3:12])([CH3:11])[O:4][C@H:3]1[O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[C:19]([NH:25][C:26](=[O:28])[CH3:27])[C:20](=[O:24])[O:21]2)=[CH:16][CH:15]=1.[CH3:29][OH:30]>C(Cl)Cl>[CH3:10][O:9][C@H:6]1[C:5]([CH3:11])([CH3:12])[O:4][C@@H:3]([O:13][C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([NH:25][C:26](=[O:28])[CH3:27])[C:20](=[O:24])[O:21]3)=[CH:16][CH:15]=2)[C@@H:2]2[O:1][C:29](=[O:30])[O:8][C@H:7]12

Participants

4

Reactant 2

HCID 887MethanolHCID 11682632HCID 11682632, compound

Product 1

HCID 11567942HCID 11567942, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

More specifically, triethylamine (0.2 mL) was added to a solution of noviosylated coumarin (45 mg, 0.10 mmol) in methanol (2 mL) at 25° C. After stirring for 48 hours, the solvent was evaporated and the residue purified by preparative TLC (SiO2, DCM-acetone; 4:1) to afford KU-1/A4 (35 mg, 0.086 mmol, 83%) as a white solid. N-(7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyl-tetrahydro-2H-pyran-2-yloxy)-2-oxo-2H-chromen-3-yl)acetamide (KU-1/A4). [α]25D=−351.6° (c, 0.06, 50% MeOH in CH2Cl2); 1HNMR (CD3OD 400 MHz) δ 8.58 (s, 1H), 7.51 (d, J=8.3 Hz, 1H), 7.03 (s, 1H), 7.02 (d, J=8.3 Hz, 1H), 5.55 (d, J=2.3 Hz, 1H), 4.10 (dd, J=3.3, 9.6 Hz, 1H), 4.03 (dd, J=2.4, 3.3 Hz, 1H), 3.60 (s, 3H), 3.38 (d, J=9.6 Hz, 1H), 2.21 (s, 3H), 1.30 (s, 3H), 1.13 (s, 3H); 13CNMR (CD3OD 100 MHZ) δ 171.6, 158.9, 158.8, 151.8, 128.9, 125.7, 122.5, 114.3, 114.1, 103.1, 99.2, 84.2, 78.8, 71.5, 68.4, 61.1, 28.2, 22.9, 22.4; IR (film) νmax 3326, 1714, 1674, 1613, 1558, 1553, 1108 cm−1; HRMS (FAB+) m/z 394.1492 (M+H+, C19H24O8 requires 394.1502).

Sources & evidence

ORD record
ord-680271e7c0434fab8354d121e596b71c
Source dataset
uspto-grants-2011_06
Patent number
US07960353B2

Reaction notes

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