Trifluoroacetic acid → HCID 68277224, compound

HRID 334425Notes

Reaction equation

HRID 334425 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C:21]2[CH:33]=[CH:32][C:24]([C:25]([O:27]C(C)(C)C)=[O:26])=[C:23]([NH:34][CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH:22]=2)[CH2:17]1)=O)(C)(C)C>ClCCl>[NH2:15][C@H:16]1[CH2:20][CH2:19][N:18]([C:21]2[CH:33]=[CH:32][C:24]([C:25]([OH:27])=[O:26])=[C:23]([NH:34][CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH:22]=2)[CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86680566HCID 86680566, compound

Product 1

HCID 68277224HCID 68277224, compoundYield 137.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

19.7 ml (25 eq) of trifluoroacetic acid is added to a solution of 4.72 g (10.23 mmol) of tert-butyl(S)-4-(3-(tert-butoxycarbonylamino)pyrrolidin-1-yl)-2-(tetrahydro-2H-pyran-4-ylamino)benzoate in 100 ml of dichloromethane. The reaction medium is stirred at room temperature for 30 hours. The solvents are evaporated and the residue is redissolved in diethyl ether and triturated until a solid is obtained. The solid formed is filtered and dried under vacuum to yield 4.3 g (100%) of a yellow powder of (S)-4-(3-aminopyrrolidin-1-yl)-2-(tetrahydro-2H-pyran-4-ylamino)benzoic acid in the form of a trifluoroacetic acid salt.

Workup

  1. customThe solvents are evaporated
  2. dissolutionthe residue is redissolved in diethyl ether
  3. customtriturated until a solid
  4. customis obtained
  5. customThe solid formed
  6. filtrationis filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-deff71042f234b39820482b3def6911c
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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