Sodium Hydroxide → HCID 86744699, compound

HRID 1084432Notes

Reaction equation

HRID 1084432 reaction equation
[OH:1][CH:2]([CH2:9][CH:10]([OH:34])/[CH:11]=[CH:12]/[C:13]1[N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[Na+:36]>CO>[OH:1][CH:2]([CH2:9][CH:10]([OH:34])/[CH:11]=[CH:12]/[C:13]1[N:14]([CH:31]([CH3:32])[CH3:33])[C:15](=[O:30])[C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][C:4]([O-:6])=[O:5].[Na+:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86744700HCID 86744700, compound

Product 1

HCID 86744699HCID 86744699, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of a 1:1 mixture of the erythro- and threo-diastereoisomers of ethyl (E)-3,5-dihydroxy-7-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]hept-6-enoate (0.18 g; prepared as described in Example 4) in methanol, (10 ml) was treated with aqueous sodium hydroxide solution (2.0M; 0.77 ml) at room temperature. After 90 minutes the solution was evaporated to dryness and the residue was azeotroped on the rotary evaporator with ethyl acetate (2×20 ml). The residue was triturated with diethyl ether (25 ml) and the product was filtered off, to give sodium (E)-3,5-dihydroxy-7-[4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl]hept-6-enoate in the form of a pale yellow solid (0.18 g). [Elemental analysis: C, 58.4; H, 5.55; N, 2.62; H2O, 10.0%; calculated for C25H25O5NFNa:3 H2O: C, 58.25; H, 6.06; N, 2.72; H2O, 10.49%].

Workup

  1. customAfter 90 minutes the solution was evaporated to dryness
  2. customthe residue was azeotroped on the rotary evaporator with ethyl acetate (2×20 ml)
  3. customThe residue was triturated with diethyl ether (25 ml)
  4. filtrationthe product was filtered off

Sources & evidence

ORD record
ord-76c04b788f5148959f4ba297d2ebfb7c
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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