Water → HCID 68315318, compound

HRID 2202144Notes

Reaction equation

HRID 2202144 reaction equation
C[O:2][C:3]([C@@:5]12[C:11]([CH3:13])([CH3:12])[C@@H:8]([CH2:9][CH2:10]1)[CH:7]=[C:6]2[C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22]([CH3:30])([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:23])=[CH:16][C:15]=1[O:31][CH3:32])=[O:4].[Li+].[OH-].O>CO.O>[CH3:32][O:31][C:15]1[CH:16]=[C:17]([C:22]([CH3:30])([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:23])[CH:18]=[C:19]([O:20][CH3:21])[C:14]=1[C:6]1[C@:5]2([C:3]([OH:4])=[O:2])[C:11]([CH3:13])([CH3:12])[C@H:8]([CH:7]=1)[CH2:9][CH2:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68315188HCID 68315188, compound

Product 1

HCID 68315318HCID 68315318, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Methyl ester 11a (HU-911) 0.103 g (0.233 mmol) and LiOH 0.111 g (4.66 mmol) in 2 ml of MeOH/H2O 3:1 were heated at 200° C. over 48 hrs in a screwed vial under air atmosphere. Water was added to the reaction mixture and extracted several times with ether. Organic phases were collected, dried over MgSO4 and concentrated in vacuo. The product was purified by preparative TLC (hexane/ethyl acetate) to give yellow solid 0.026 g (26%). mp 101-102° C.; 1H NMR (300 MHz, CDCl3) δ ppm 6.46 (s, 2H), 6.32 (d, J=3.40 Hz, 1H), 3.71 (s, 6H), 2.46 (t, J=3.44 Hz, 1H), 2.38-2.44 (m, 1H), 1.80-2.03 (m, 1H), 1.53-1.58 (m, 2H), 1.26 (s, 6H), 1.16-1.24 (m, 7H), 1.14 (s, 3H), 1.03-1.12 (m, 3H), 1.00 (s, 3H), 0.85 (t, J=6.74 Hz, 3H). Exact mass calculated for C28H42O4 m/e 428.29. found 428.98. Anal. calcd. for C28H42O4: C, 75.66; H, 9.41. Found: C, 75.50; H, 9.48.

Workup

  1. extractionextracted several times with ether
  2. customOrganic phases were collected
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by preparative TLC (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4e9325da535e459fb6ab0bd7bad8d5d1
Source dataset
uspto-grants-2016_06
Patent number
US09365534B2

Reaction notes

Loading…