Hydrochloric Acid → HCID 15479558, compound

HRID 1954008Notes

Reaction equation

HRID 1954008 reaction equation
[OH-].[Li+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([P:33]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)(=[O:42])[O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[P:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)([O:5]C)=[O:4].Cl>O.O1CCOCC1>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([P:33]([O:43][CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)(=[O:42])[O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[P:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:24])[O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:9][CH:8]=1)([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 15479556HCID 15479556, compound

Product 1

HCID 15479558HCID 15479558, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of lithium hydroxide (84 mg, 2.0 mmol) in water (1.0 mL) is added to a solution of methyl ester 2 (455 mg, 0.6 mmol) in 1,4-dioxane (1.0 mL) at room temperature. The mixture is stirred at room temperature for 5 hours and a 1N solution of HCl (10 mL) is added. Dioxane is evaporated under reduced pressure and the mixture is diluted with EtOAc (20 mL). The separated aqueous layer is extracted with EtOAc (3×50 mL) and the combined organic layers are washed (brine), dried (MgSO4 anh.), filtered and evaporated. Flash-chromatography (HOAc:EtOH:EtOAc (0.1:1:9)) of the residue gives carboxylic acid 4 (210 mg, 48%). 1H NMR (CDCl3): δ 9.65 (1H, br. s), 7.98 (2H, d, J=8.1 Hz), 7.26 (20H, s), 7.13 (2H, d, J=8.1 Hz), 4.95 (8H, m), 3.31 (2H, td, J=16.7, 6.4 Hz), 2.82 (1H, tt, J=24.0, 6.4 Hz). 13C NMR (CDCl3): δ 170.0, 144.6 (t, J=7.6 Hz), 135.9, 135.8, 130.1, 129.0, 128.6, 128.5, 128.4, 128.3, 128.2, 128.1, 68.3 (dd, J=19.6, 6.5 Hz), 39.4 (t, J=133.2 Hz), 31.2 (br. s).

Workup

  1. customDioxane is evaporated under reduced pressure
  2. additionthe mixture is diluted with EtOAc (20 mL)
  3. extractionThe separated aqueous layer is extracted with EtOAc (3×50 mL)
  4. washthe combined organic layers are washed (brine)
  5. dry with materialdried (MgSO4 anh.)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-de8d4daf271e4f99b971064ea78281c9
Source dataset
uspto-grants-2000_09
Patent number
US06121253

Reaction notes

Loading…