Trifluoroacetic acid → HCID 68277224, compound

HRID 1487397Notes

Reaction equation

HRID 1487397 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-493f5bcba0644689a53979b5d69af807
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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