Hydrochloric Acid → (S,E)-3-Hydroxy-7-(tritylthio)hept-4-enoic acid

HRID 1915969Notes

Reaction equation

HRID 1915969 reaction equation
[OH:1][C@H:2](/[CH:15]=[CH:16]/[CH2:17][CH2:18][S:19][C:20]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:3][C:4](N1[C@H](C(C)C)CSC1=S)=[O:5].[Li+].[OH-].Cl.CC[O:44]C(C)=O>C1COCC1.O>[OH:1][C@H:2](/[CH:15]=[CH:16]/[CH2:17][CH2:18][S:19][C:20]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:3][C:4]([OH:44])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 11421639(S,E)-3-hydroxy-1-((R)-4-isopropyl-2-thioxothiazolidin-3-yl)-7-(tritylthio)hept-4-en-1-one

Product 1

HCID 11711429(S,E)-3-Hydroxy-7-(tritylthio)hept-4-enoic acidYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

At 0° C. to a solution of (S,E)-3-hydroxy-1-((R)-4-isopropyl-2-thioxothiazolidin-3-yl)-7-(tritylthio)hept-4-en-1-one (934 mg, 1.66 mmol, prepared according to the procedure in Yurek-George, A. et al, J. Am. Chem. Soc. 2004, 126, 1030) in THF (30 mL) was added a solution of LiOH (196.1 mg, 8.19 mmol) in H2O (10 mL). The reaction mixture was allowed to warm to rt over 1 h, whereupon 1M HCl was added until the pH reached 2. EtOAc (30 mL) was then added and the layers were separated. The aqueous layer was extracted with EtOAc (20 mL) the organic layers were combined, dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography (eluant 3:7-1:1-1:0 EtOAc/Hexane) gave the 3 as a white solid (600 mg, 1.43 mmol, 86%).

Workup

  1. additionwas added until the pH
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc (20 mL) the organic layers
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (eluant 3:7-1:1-1:0 EtOAc/Hexane)

Sources & evidence

ORD record
ord-e642628bb9aa49a9b58672aeacfbc352
Source dataset
uspto-grants-2013_12
Patent number
US08614193B2

Reaction notes

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