Trifluoroacetic acid → HCID 69586875, compound

HRID 2216119Notes

Reaction equation

HRID 2216119 reaction equation
C(OC([NH:8][C:9](=[NH:47])[C:10]1[S:14][C:13]([S:15][CH3:16])=[C:12]([S:17]([C:20]2[CH:21]=[C:22]([C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=3[NH:33][C:34](=[O:46])[NH:35][CH2:36][CH2:37][NH:38][C:39](=[O:45])[NH:40][CH2:41][C:42]([OH:44])=[O:43])[CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:11]=1)=O)(C)(C)C.[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51]>C(Cl)Cl>[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[C:9]([C:10]1[S:14][C:13]([S:15][CH3:16])=[C:12]([S:17]([C:20]2[CH:21]=[C:22]([C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:27]=3[NH:33][C:34](=[O:46])[NH:35][CH2:36][CH2:37][NH:38][C:39](=[O:45])[NH:40][CH2:41][C:42]([OH:44])=[O:43])[CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:11]=1)(=[NH:8])[NH2:47]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 145857659HCID 145857659, compound

Product 1

HCID 69586875HCID 69586875, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of {3-[2-(3-{3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-2-yl}-ureido)-ethyl]-ureido}-acetic acid ((Example 196: step b) 0.025 g, 0.035 mmol) in CH2Cl2 (10 mL) was treated with trifluoroacetic acid (1.00 mL) and stirred at room temperature 1.2 h. Solvents were removed in vacuo. Preparatory HPLC (10–80% acetonitrile in 1% TFA/water over 30 min.) afforded the product [3-(2-{3-[3′-(5-carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-yl]-ureido}-ethyl)-ureido]-acetic acid trifluoroacetate (0.013 g, 60%) as a white glassy solid. 1H NMR (CD3CN): δ 8.099 (s, 1H), 8.048 (d, 1H, J=9.6 Hz), 7.815 (t, 1H, J=1.6 Hz), 7.709 (t, 1H, J=8.0 Hz), 7.575 (d, 1H, J=7.6 Hz), 7.498 (d, 1H, J=8.0 Hz), 7.295 (t, 1H, J=7.6 Hz), 7.161 (d, 1H, J=8.0 Hz), 3.756 (s, 2H), 2.979 (s br, 4H), 2.681 (s, 3H), 2.079 (s, 3H).

Workup

  1. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-9d775fca25254875a3a698d8d5317289
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

Loading…