4-[({(2S,4S)-1-(4-carbamimidoylbenzoyl)-4-[4-(methylsulfonyl)-1-piperazinyl]-2-pyrrolidinyl}carbonyl)amino]benzoic acid bis(trifluoroacetate) → ethyl 4-[({(2S,4S)-1-(4-carbamimidoylbenzoyl)-4-[4-(methylsulfonyl)-1-piperazinyl]-2-pyrrolidinyl}carbonyl)amino]benzoate bis(trifluoroacetate)

HRID 1053850Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[C:15]([C:18]1[CH:52]=[CH:51][C:21]([C:22]([N:24]2[CH2:28][C@@H:27]([N:29]3[CH2:34][CH2:33][N:32]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:31][CH2:30]3)[CH2:26][C@H:25]2[C:39]([NH:41][C:42]2[CH:50]=[CH:49][C:45]([C:46]([OH:48])=[O:47])=[CH:44][CH:43]=2)=[O:40])=[O:23])=[CH:20][CH:19]=1)(=[NH:17])[NH2:16]>C(O)C.S(=O)(=O)(O)O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[C:15]([C:18]1[CH:19]=[CH:20][C:21]([C:22]([N:24]2[CH2:28][C@@H:27]([N:29]3[CH2:34][CH2:33][N:32]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:31][CH2:30]3)[CH2:26][C@H:25]2[C:39]([NH:41][C:42]2[CH:43]=[CH:44][C:45]([C:46]([O:48][CH2:2][CH3:3])=[O:47])=[CH:49][CH:50]=2)=[O:40])=[O:23])=[CH:51][CH:52]=1)(=[NH:16])[NH2:17]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of compound prepared in Example 20 (500 mg) in ethanol (25 mL) was added concentrated sulfuric acid (20 drops) at 0° C. The resulting mixture was stirred at 60° C. for 44 h whereupon the mixture was concentrated in vacuo. The resulting residue was purified by Prep-HPLC (0.1% TFA containing CH3CN—H2O gradient) to provide the title compound (307 mg).

Workup

concentrationwas concentrated in vacuo
customThe resulting residue was purified by Prep-HPLC (0.1% TFA containing CH3CN—H2O gradient)

Sources & evidence

ORD record: ord-b00793d14a9f4ca69bc7361225114fc7
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394250B2

Reaction notes

Loading…