HCID 68792675, compound → HCID 24853496, compound

HRID 1713587Notes

Reaction equation

HRID 1713587 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@:6]21[C:32]1[C:27](=[CH:28][C:29]([Cl:42])=[C:30]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([CH2:40][CH3:41])=[CH:36][CH:35]=3)[CH:31]=1)[O:26][CH2:25][CH2:24]2)(=O)C.O(C)[Li]>CO>[Cl:42][C:29]1[CH:28]=[C:27]2[O:26][CH2:25][CH2:24][C@@:6]3([C@H:5]([OH:4])[C@@H:10]([OH:11])[C@H:9]([OH:15])[C@@H:8]([CH2:19][OH:20])[O:7]3)[C:32]2=[CH:31][C:30]=1[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([CH2:40][CH3:41])=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 68792675HCID 68792675, compoundHCID 178419045HCID 178419045, compound

Product 1

HCID 24853496HCID 24853496, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(2′S,3′R,4′S,5′R,6′R)-6′-(Acetoxymethyl)-7-chloro-6-(4-ethylbenzyl)-3′,4′,5′,6′-tetrahydrospiro[chroman-4,2′-pyran]-3′,4′,5′-triyl triacetate (19) (9.6 mg, 0.02 mmol) was dissolved in MeOH (0.2 mL) and treated with LiOMe (20 μL of a 1M solution in MeOH). After 24 h, the reaction mixture was filtered through a syringe filter and concentrated, then passed through a small SiO2 column, eluting with 5% MeOH/CH2Cl2 to provide a film (5.8 mg, 83%). 1H NMR (300 MHz, CD3OD) δ ppm: 7.37 (s, 1H), 7.05 (s, 4H), 6.79 (s, 1H), 4.33 (m, 1H), 4.13 (m, 1H), 3.97 (s, 2H), 3.78 (m, 2H), 3.48-3.62 (m, 3H), 3.33 (m, 2H), 2.57 (q, J=15, 7.8 Hz, 2H), 2.33-2.42 (m, 1H), 2.13-2.21 (m, 1H), 1.19 (t, J=7.5 Hz, 3H). LC/MS 100% (ELSD) tR=1.99 min, calcd for C23H27ClO6: 434.15, found 434.15 (M+Na)+.

Workup

  1. filtrationthe reaction mixture was filtered through a syringe
  2. filtrationfilter
  3. concentrationconcentrated
  4. washeluting with 5% MeOH/CH2Cl2
  5. customto provide a film (5.8 mg, 83%)

Sources & evidence

ORD record
ord-42cf9526f2b347cd91fe7b7675989f72
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

Loading…