Sodium Hydroxide → HCID 23704065, compound

HRID 1087733Notes

Reaction equation

HRID 1087733 reaction equation
[OH:1][CH:2]([CH2:9][CH:10]([OH:35])/[CH:11]=[CH:12]/[C:13]1[C:14]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17][N:16]2[C:25]=1[CH:26]([CH3:28])[CH3:27])[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[Na+:37]>O.CO>[OH:1][CH:2]([CH2:9][CH:10]([OH:35])/[CH:11]=[CH:12]/[C:13]1[C:14]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17][N:16]2[C:25]=1[CH:26]([CH3:28])[CH3:27])[CH2:3][C:4]([O-:6])=[O:5].[Na+:37]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23166911HCID 23166911, compound

Product 1

HCID 23704065HCID 23704065, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of a 3:2 mixture of the erythro- and threo-isomers of ethyl (E)-3,5-dihydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazin-2-yl)-hept -6-enoate (0.26 g; prepared as described in Example 1) and sodium hydroxide (22 mg) in water (1.0 ml) and methanol (10 ml) was stirred at the ambient temperature under an atmosphere of argon for 3 hours. The solution was then evaporated in vacuo and the residue was dried by treatment twice with methanol (2×10 ml) and once with diethyl ether (10 ml) followed each time by evaporation in vacuo, finally drying under high vacuum, to give sodium (E)-3,5-dihydroxy-7-(3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazin-2-yl)-hept-6-enoate (0.21 g) in the form of a yellow solid, m.p. 209°-215° C. [Elemental analysis: C, 65.8; H, 6.1; N, 5.4; H2O, 4.9%; calculated for C27H27N2O4Na:1.5H2O: C, 65.7; H, 6.13; N, 5.7; H2O, 5.5%; NMR (in a mixture of DMSO-d6 and D2O): 1.10-1.32 (2 H, m), 1.5 (6 H, d, J=7 Hz), 1.7-2.1 (2 H, m), 3.50-3.86 (2 H, m), 4.02-4.16 (1 H, m), 5.28 and 5.36 (1 H, two dd, J=16 Hz, 6 Hz), 6.46 (1 H, dd, J=16 Hz, 1 Hz), 7.16-7.60 (8 H, m), 7.78-7.88 (1 H, m), 8.57 (1 H, s)].

Workup

  1. additionA solution of a 3:2 mixture of the erythro-
  2. customThe solution was then evaporated in vacuo
  3. dry with materialthe residue was dried by treatment twice with methanol (2×10 ml) and once with diethyl ether (10 ml)
  4. customby evaporation in vacuo
  5. customfinally drying under high vacuum

Sources & evidence

ORD record
ord-d0e2fe34a8c646f29757bdd44b4a5296
Source dataset
uspto-grants-1990_10
Patent number
US04960775

Reaction notes

Loading…