Hydrochloric Acid → HCID 59554915, compound

HRID 1695903Notes

Reaction equation

HRID 1695903 reaction equation
[CH2:1]([N:6]1[C:10](=[O:11])[CH:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:8][CH:7]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:2][CH:3]([CH3:5])[CH3:4].[Li+].[CH3:25][Si]([N-][Si](C)(C)C)(C)C.Cl>C1COCC1>[CH2:1]([N:6]1[C:10](=[O:11])[CH:9]([CH:12]([CH3:25])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:8][CH:7]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 59554901Ethyl 2-(3-isopentyl-4-oxo-2-phenylthiazolidin-5-yl)acetate

Product 1

HCID 59554915HCID 59554915, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 2-(3-isopentyl-4-oxo-2-phenylthiazolidin-5-yl)acetate (84 mg, 0.25 mmol) in THF at 0° C. was added LiHMDS (0.28 ml of 1 N, 0.28 mmol) dropwise and the reaction mixture was stirred from 0° C. to RT over 16 hours. The reaction mixture was poured in to 1 N HCl and extracted with EtOAc (4×). The organics were combined, dried (MgSO4) and evaporated to dryness. Purification by preparative TLC (7:1; Hx:EtOAc) gave the desired product as an oil (12 mg).

Workup

  1. extractionextracted with EtOAc (4×)
  2. dry with materialdried (MgSO4)
  3. customevaporated to dryness
  4. customPurification by preparative TLC (7:1; Hx:EtOAc)

Sources & evidence

ORD record
ord-b0acb434d2e3474dba25dc70ef2ce6e2
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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