Trifluoroacetic acid → HCID 22115362, compound

HRID 1276366Notes

Reaction equation

HRID 1276366 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][C:22](=[O:39])[CH2:23][S:24][C:25]2[N:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)=[CH:27][N:26]=2)[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[NH:15]1[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][C:22](=[O:39])[CH2:23][S:24][C:25]2[N:26]=[CH:27][C:28]([C:31]3[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=3)=[CH:29][N:30]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22115331HCID 22115331, compound

Product 1

HCID 22115362HCID 22115362, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat anhydrous trifluoroacetic acid (3 mL) was added to a solution of N-(1-tert-butoxycarbonylpyrrolidin-3-(RS)-ylmethyl)-2-[5-(4-methoxyphenyl)pyrimidin-2-ylthio]-acetamide (0.60 g, 1.3 mmol) in methylene chloride (20 mL) at room temperature. Gas evolution was apparent immediately upon addition of the acid. After 30 min., the reaction mixture was concentrated using a Teflon dryvac system, and was then further concentrated under high vacuum to give N-(pyrrolidin-3-(RS)-ylmethyl)-2-[5-(4-methoxyphenyl)pyrimidin-2-ylthio]acetamide which was dissolved in 10 mL dichloroethane (0.13 mmol/mL).

Workup

  1. additionGas evolution was apparent immediately upon addition of the acid
  2. concentrationthe reaction mixture was concentrated
  3. concentrationwas then further concentrated under high vacuum

Sources & evidence

ORD record
ord-c1cb89ec36f34260829511627b7db57f
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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