Trifluoroacetic acid → 4-[({(2S,4S)-1-[(1-carbamimidoyl-4-piperidinyl)carbonyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-2-pyrrolidinyl}carbonyl)amino]benzoic acid bis(trifluoroacetate)

HRID 1053816Notes

Reaction equation

HRID 1053816 reaction equation
CC(OC([NH:8][C:9]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]([N:26]2[CH2:30][C@@H:29]([N:31]3[CH2:36][CH2:35][N:34]([S:37]([CH3:40])(=[O:39])=[O:38])[CH2:33][CH2:32]3)[CH2:28][C@H:27]2[C:41]([NH:43][C:44]2[CH:56]=[CH:55][C:47]([C:48]([O:50]C(C)(C)C)=[O:49])=[CH:46][CH:45]=2)=[O:42])=[O:25])[CH2:20][CH2:19]1)=[N:10]C(OC(C)(C)C)=O)=O)(C)C.[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60]>ClCCl>[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60].[F:57][C:58]([F:63])([F:62])[C:59]([OH:61])=[O:60].[C:9]([N:18]1[CH2:19][CH2:20][CH:21]([C:24]([N:26]2[CH2:30][C@@H:29]([N:31]3[CH2:36][CH2:35][N:34]([S:37]([CH3:40])(=[O:39])=[O:38])[CH2:33][CH2:32]3)[CH2:28][C@H:27]2[C:41]([NH:43][C:44]2[CH:45]=[CH:46][C:47]([C:48]([OH:50])=[O:49])=[CH:55][CH:56]=2)=[O:42])=[O:25])[CH2:22][CH2:23]1)(=[NH:8])[NH2:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1317363002-methyl-2-propanyl 4-[({(2S,4S)-1-{[1-(N,N'-bis{[(2-methyl-2-propanyl)oxy]carbonyl}carbamimidoyl)-4-piperidinyl]carbonyl}-4-[4-(methylsulfonyl)-1-piperazinyl]-2-pyrrolidinyl}carbonyl)amino]benzoate

Product 1

HCID 1181076974-[({(2S,4S)-1-[(1-carbamimidoyl-4-piperidinyl)carbonyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-2-pyrrolidinyl}carbonyl)amino]benzoic acid bis(trifluoroacetate)Yield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound prepared in Example 8 (0.11 g, 0.13 mmol) in dichloromethane (15 mL) at 0° C. was added trifluoroacetic acid (0.5 mL). The reaction was warmed to room temperature and stirred for 18 h. The solvent and excess trifluoroacetic acid was removed under reduced pressure. The solid was dissolved in water and lyophilized to dryness to afford the title compound (0.030 g, 40%) as an off-white solid.

Workup

  1. customThe solvent and excess trifluoroacetic acid was removed under reduced pressure
  2. dissolutionThe solid was dissolved in water

Sources & evidence

ORD record
ord-7593e35dfcb74a7ab3f40c3a06977b27
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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