tert-Butyl {2-[3-(tert-butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate → [2-(3-Phenethylamino-propylsulfanyl)-benzoimidazol-1-yl]-acetic acid

HRID 2389494Notes

Reaction equation

HRID 2389494 reaction equation
C(OC([N:8]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:9][CH2:10][CH2:11][S:12][C:13]1[N:17]([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[N:14]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[CH2:30]([NH:8][CH2:9][CH2:10][CH2:11][S:12][C:13]1[N:17]([CH2:18][C:19]([OH:21])=[O:20])[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[N:14]=1)[CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

3

Reactant 1

HCID 86620029tert-Butyl {2-[3-(tert-butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate

Product 1

HCID 86620031[2-(3-Phenethylamino-propylsulfanyl)-benzoimidazol-1-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-Butyl {2-[3-(tert-butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate (Precursor J-01b, 5.5 mg, 0.015 mmol) is dissolved in TFA/dichloromethane (1:1, 1.5 ml) and stirred at rt for 1.5 h. The solvents are evaporated under reduced pressure and the residue is dried under high vacuum, yielding the pure title compound: tR=1.51 min (LC-2), ESI-MS (pos.): m/z 370.39 [M+H]+; ESI-MS (neg.): m/z 368.42 [M−H]+.

Workup

  1. customThe solvents are evaporated under reduced pressure
  2. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-fd2501bf75f44d03860d0a11db9dd5c7
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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