Imidazole → HCID 89585238, compound

HRID 714766Notes

Reaction equation

HRID 714766 reaction equation
N1C=CN=C1.[C:6]([Si:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)Cl)([CH3:9])([CH3:8])[CH3:7].[OH:24][CH:25]([C:39]1[S:40][CH:41]=[CH:42][N:43]=1)[C@H:26]1[CH2:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:27]1>ClCCl>[Si:10]([O:24][C@@H:25]([C:39]1[S:40][CH:41]=[CH:42][N:43]=1)[C@H:26]1[CH2:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:33])[CH2:27]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Si:10]([O:24][C@H:25]([C:39]1[S:40][CH:41]=[CH:42][N:43]=1)[C@H:26]1[CH2:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:33])[CH2:27]1)([C:6]([CH3:9])([CH3:8])[CH3:7])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 89585232HCID 89585232, compound

Product 2

HCID 89585238HCID 89585238, compoundHCID 90444768HCID 90444768, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.91 g (0.102 mol) of imidazole and 26.435 ml (0.201 mol) of tert-butyldiphenylchlorosilane were added successively at 22° C. to a solution of 19 g (0.058 mol) of tert-butyl (S)-3-(hydroxythiazol-2-yl-methyl)piperidine-1-carboxylate [diastereomer mixture] in 250 ml of dichloromethane. 250 ml of ice-water were added to the reaction mixture. The organic phase was dried over sodium sulfate, filtered and evaporated. The crude product was chromatographed over silica gel, giving 3.44 g of tert-butyl (S)-3-[(R)-(tert-butyldiphenylsilanyloxy)thiazol-2-ylmethyl]piperidine-1-carboxylate (rotation value in methanol [α]20D=+28.00) and 1.19 g of tert-butyl (S)-3-[(S)-(tert-butyldiphenylsilanyloxy)thiazol-2-ylmethyl]-piperidine-1-carboxylate (rotation value in methanol [α]20D=−1.3°); HPLC/MS (M+H)+=537.

Workup

  1. dry with materialThe organic phase was dried over sodium sulfate
  2. filtrationfiltered
  3. customevaporated
  4. customThe crude product was chromatographed over silica gel

Sources & evidence

ORD record
ord-7b837307765245188f56ebec98264a82
Source dataset
uspto-grants-2015_11
Patent number
US09187469B2

Reaction notes

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