Aluminium lithium hydride → HCID 57586357, compound

HRID 2190349Notes

Reaction equation

HRID 2190349 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7][C:8]([N:10]([CH2:14][CH2:15][CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]([CH3:13])[CH3:12])=[O:9])=[N:4][C:3]=1[C:29]1[CH:38]=[CH:37][C:32]([C:33](OC)=[O:34])=[CH:31][CH:30]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:9])[N:10]([CH2:14][CH2:15][CH:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:11]([CH3:13])[CH3:12])=[N:4][C:3]=1[C:29]1[CH:38]=[CH:37][C:32]([CH2:33][OH:34])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57586345HCID 57586345, compound

Product 1

HCID 57586357HCID 57586357, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 4-(5-chloro-2-(3-(3,3-diphenylpropyl)-3-isopropylureido)thiazol-4-yl)benzoate 175 (0.424 g, 0.774 mmol) was dissolved in THF (5 mL) and cooled to 0° C. To this solution, lithium aluminium hydride (2M solution in THF, 0.77 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 1 h, quenched with Rochelle's salt solution and then extracted with ethyl acetate. Organics were concentrated and purified by column chromatography on silica using 1:1 EtOAc:Hexane. Product 176 was obtained as a solid (0.38 g, 95%). Mass spectrum: calculated for C29H30ClN3O2S 519.2; found 520.2 (M+H).

Workup

  1. customquenched with Rochelle's salt solution
  2. extractionextracted with ethyl acetate
  3. concentrationOrganics were concentrated
  4. custompurified by column chromatography on silica using 1:1 EtOAc

Sources & evidence

ORD record
ord-67579905963a47f79a9af5c14aedcd82
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

Loading…