HCID 131720360, compound → HCID 86751751, compound

HRID 1940455Notes

Reaction equation

HRID 1940455 reaction equation
[C:1]([C@:4](CO)([OH:25])[C@:5](C(=O)C)([OH:21])[C@:6](C(=O)C)([OH:17])[C@@:7](C(=O)C)([OH:13])[C:8]([CH2:10][CH:11]=[CH2:12])=[O:9])(=[O:3])C>[OH-].[Na+]>[CH2:10]([C:8]([C@@H:7]([C@H:6]([C@H:5]([C@@H:4]([CH2:1][OH:3])[OH:25])[OH:21])[OH:17])[OH:13])=[O:9])[CH:11]=[CH2:12]

Participants

3

Reactant 1

HCID 131720360HCID 131720360, compound

Product 1

HCID 86751751HCID 86751751, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Compound 1 (23 g) was dissolved in 4N NaOH solution (100 mL) and stirred for 2 hr. The reaction mixture was extracted with ether. The aqueous layer was acidified with Dowex-H resin. The resin was removed by filtration and the filtrate was lyophilized to give the deprotected derivative 2 as a white powder. This was recrystallized in ethyl acetate-methanol (7:3) to give crystals (7.0 g). 1H NMR (CD3OD): δ8.2-8.90, m, 1H, CH2CH=CH2 ; 5.12-5.09, dd, 2H, CH2CH=CH2 ; 3.99-4.01, m, 1H, H-1; 3.80-3.84, m, 1H, H-2; 3.87-3.62, mm, 3H, H,4,5,6: 13C NMR (CD3OD): 136.73, 116.86, 75.66, 74.02, 71.91, 70.11, 70.00, 61.97, 31.03: [α]D =+106.45 (C 1.03, methanol).

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. customThe resin was removed by filtration

Sources & evidence

ORD record
ord-8360af7eef234659a0cc5922cc044d60
Source dataset
uspto-grants-1997_12
Patent number
US05700458

Reaction notes

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