Trifluoroacetic acid → HCID 178512988, compound

HRID 987214Notes

Reaction equation

HRID 987214 reaction equation
C([O:5][C:6](=[O:42])[C@@H:7]([NH:32][S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[O:35])=[O:34])[CH2:8][NH:9][C:10]([NH:12][C:13]1[C:22](=[O:23])[N:21]2[C:16]([CH:17]=[CH:18][C:19]([O:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]([NH2:31])=[NH:30])=[CH:20]2)=[CH:15][CH:14]=1)=[O:11])(C)(C)C.[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46]>ClCCl>[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[C:36]1([S:33]([NH:32][C@@H:7]([CH2:8][NH:9][C:10]([NH:12][C:13]2[C:22](=[O:23])[N:21]3[C:16]([CH:17]=[CH:18][C:19]([O:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]([NH2:31])=[NH:30])=[CH:20]3)=[CH:15][CH:14]=2)=[O:11])[C:6]([OH:42])=[O:5])(=[O:35])=[O:34])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451197HCID 178451197, compound

Product 1

HCID 178512988HCID 178512988, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension (S)-2-benzenesulfonylamino-3-{3-[7-(3-guanidino-propoxy)-4-oxo-4H-quinolizin-3-yl]-ureido}-propionic acid tert-butyl ester (30 mg, 0.049 mmol) in dichloromethane (4 mL) was added trifluoroacetic acid (6 mL). The mixture was stirred overnight, evaporated to dryness and triturated in ether (3X) and hexane (1X). Compound IX was purified by preparative HPLC using 1:1 MeCN:H2O as eluent and characterized by 1H NMR (400 MHz) (CD3OD) d: 8.51 (d, 1H, J=8.5 Hz), 8.45 (s, 1H), 7.98-7.85 (m, 2H), 7.63 (d, 1H, J=9 Hz), 7.49-7.47 (m, 3H), 7.10 (d, 1H, J=9 Hz), 6.98 (d, 1H, J=8.5 Hz), 4.20 (t, 2H, J=5.5 Hz), 4.03-4.01 (m, 1H), 3.65-3.62 (m, 1H), 3.49-3.42 (m, 3H), 2.20-2.14 (m, 2H)

Workup

  1. customevaporated to dryness
  2. customtriturated in ether (3X)
  3. customCompound IX was purified by preparative HPLC

Sources & evidence

ORD record
ord-74c7c1f2f555401c9e0d10afc918a03c
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

Loading…