Trifluoroacetic acid → (s)-n-{(s)-1-Cyclohexyl-2-[(s)-2-(indan-2-yloxymethyl)-pyrrolidin-1-yl]-2-oxo-ethyl}-2-methylamino-propionamide

HRID 222500Notes

Reaction equation

HRID 222500 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]([C:11](=[O:38])[NH:12][C@@H:13]([CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[CH2:21][O:22][CH:23]1[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1)=[O:15])[CH3:10])C)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:32]1([C@H:13]([NH:12][C:11](=[O:38])[C@@H:9]([NH:7][CH3:6])[CH3:10])[C:14]([N:16]2[CH2:20][CH2:19][CH2:18][C@H:17]2[CH2:21][O:22][CH:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24]2)=[O:15])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67004135HCID 67004135, compound

Product 1

HCID 11704883(s)-n-{(s)-1-Cyclohexyl-2-[(s)-2-(indan-2-yloxymethyl)-pyrrolidin-1-yl]-2-oxo-ethyl}-2-methylamino-propionamideYield 21.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

((S)-1-{(S)-1-Cyclohexyl-2-[(S)-2-(indan-2-yloxymethyl)-pyrrolidin-1-yl]-2-oxo-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester (Q) (0.54 g, 1 mmol) is dissolved in DCM (8 mL) and treated with trifluoroacetic acid (4 mL) for 45 minutes. The reaction mixture is concentrated in vacuo, purified by preparative reverse-phase hplc to give 0.096 g of the methylamine (34) as a clear gum: LCMS (ES) 442.26 (MH+).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. custompurified by preparative reverse-phase hplc

Sources & evidence

ORD record
ord-900a299fce3d48b989ad4cbdedbf818e
Source dataset
uspto-grants-2012_06
Patent number
US08207183B2

Reaction notes

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