Hydrochloric Acid → 5-(3-((1R,2R,3R,5R)-5-Chloro-2-((3S 8R,E)-3,8-dihydroxynon-1-en-1-yl)-3-hydroxycyclopentyl)propyl)thiophene-2-carboxylic acid

HRID 628943Notes

Reaction equation

HRID 628943 reaction equation
[OH-].[Li+].[Cl:3][C@H:4]1[C@H:8]([CH2:9][CH2:10][CH2:11][C:12]2[S:16][C:15]([C:17]([O:19]C)=[O:18])=[CH:14][CH:13]=2)[C@@H:7](/[CH:21]=[CH:22]/[C@@H:23]([OH:31])[CH2:24][CH2:25][CH2:26][CH2:27][C@H:28]([OH:30])[CH3:29])[C@H:6]([OH:32])[CH2:5]1.Cl>O.C1COCC1>[Cl:3][C@H:4]1[C@H:8]([CH2:9][CH2:10][CH2:11][C:12]2[S:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][CH:13]=2)[C@@H:7](/[CH:21]=[CH:22]/[C@@H:23]([OH:31])[CH2:24][CH2:25][CH2:26][CH2:27][C@H:28]([OH:30])[CH3:29])[C@H:6]([OH:32])[CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 118048192HCID 118048192, compound

Product 1

HCID 1180367495-(3-((1R,2R,3R,5R)-5-Chloro-2-((3S 8R,E)-3,8-dihydroxynon-1-en-1-yl)-3-hydroxycyclopentyl)propyl)thiophene-2-carboxylic acidYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (1.2 mL of a 0.5N solution in H2O, 0.605 mmol) was added to a solution of the ester 31 (111 mg, 0.242 mmol) in THF (0.5 mL) at 23° C. After stirring for 24 h the reaction mixture was acidified with 1N HCl and extracted with EtOAc. The organic portion was washed with brine (2×), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 4:1 CH2Cl2/MeOH) provided 90 mg (84%) of the free acid 33 (see Scheme 5).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic portion was washed with brine (2×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash column chromatography (silica gel, 4:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-a1743ef62de44a6ab1e32cc74915fc9d
Source dataset
uspto-grants-2016_04
Patent number
US09315486B2

Reaction notes

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