Trifluoroacetic acid → (1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylic acid

HRID 926006Notes

Reaction equation

HRID 926006 reaction equation
[Si:1]([O:18][C@H:19]1[CH2:24][C@@H:23]([C:25]([O:27]C(C)(C)C)=[O:26])[C@H:22]([C:32](=[O:41])[N:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40])[CH3:34])[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Si:1]([O:18][C@H:19]1[CH2:24][C@@H:23]([C:25]([OH:27])=[O:26])[C@H:22]([C:32](=[O:41])[N:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40])[CH3:34])[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58282736(1R,2R,5R)-tert-butyl 5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylate

Product 1

HCID 58282725(1R,2R,5R)-5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylic acidYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 39 (1.07 mmol) in anhydrous DCM (70 mL) was added TFA (42.6 mmol) slowly. The reaction mixture was stirred at room temperature for 16 hrs. The reaction mixture was concentrated and purified by silica gel chromatography (DCM/MeOH) to yield compound 40 as a yellow oil in 48% yield. MS (ESI, EI+): m/z=522 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-96056136ac7a407cb903af1fadabd026
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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