Hydrochloric Acid → HCID 42636430, compound

HRID 1092449Notes

Reaction equation

HRID 1092449 reaction equation
C([O:4][C@H:5]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=3)[CH:12]=2)[C@@H:9]([O:28]C(=O)C)[C@H:8]([CH2:32][O:33]C(=O)C)[C@@H:7]([O:37]C(=O)C)[C@@H:6]1[O:41]C(=O)C)(=O)C.[OH-].[Na+].Cl>CO>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C@@H:10]2[C@@H:9]([OH:28])[C@H:8]([CH2:32][OH:33])[C@@H:7]([OH:37])[C@H:6]([OH:41])[C@H:5]2[OH:4])=[CH:12][C:13]=1[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25](=[O:27])[CH3:26])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57741110HCID 57741110, compound

Product 1

HCID 42636430HCID 42636430, compoundYield 149.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1S,2R,3R,4S,5R,6R)-4-(acetoxymethyl)-6-(3-(4-acetylbenzyl)-4-chlorophenyl)cyclohexane-1,2,3,5-tetrayl tetraacetate (38) (300 mg, 47.6 μmol) in MeOH (5 mL) was added sodium hydroxide (29 mg, 72 μmol) and stirred for 1.5 h under reflux. The mixture was acidified to pH 6 with 1 N hydrochloric acid and the solvents were removed under reduced pressure. The residue was purified by preparative HPLC to provide 30 mg of the desired compound. 1H-NMR (400 MHz, CD3OD): δ 7.90 (2H, d, J=8.4 Hz), 7.35 (3H, m), 7.22 (H, d, J=1.6 Hz), 7.18 (1H, d, J=8.4, 1.6 Hz), 4.17 (2H, s), 3.91 (2H, d, J=3.2 Hz), 3.66 (1H, t, J=10.4 Hz), 3.49-3.40 (2H, m), 3.30 (1H, m), 2.57-2.52 (4H, m), 1.55-1.50 (1H, m); MS (ESI+): 421 [M+H]+, 443 [M+Na]+, (ESI−): 465 [M+HCOO]−.

Workup

  1. temperatureunder reflux
  2. customthe solvents were removed under reduced pressure
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-719879a3abaf4fde8289837093c8cecb
Source dataset
uspto-grants-2012_03
Patent number
US08129434B2

Reaction notes

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