Trifluoroacetic acid → HCID 56626233, compound

HRID 987213Notes

Reaction equation

HRID 987213 reaction equation
C([O:5][C:6](=[O:49])[C@@H:7]([NH:39][S:40]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=[O:42])=[O:41])[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]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:30])=[CH:20]2)=[CH:15][CH:14]=1)=[O:11])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:43]1([S:40]([NH:39][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]([O:31][CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:30])=[CH:20]3)=[CH:15][CH:14]=2)=[O:11])[C:6]([OH:49])=[O:5])(=[O:41])=[O:42])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 56635694HCID 56635694, compound

Product 1

HCID 56626233HCID 56626233, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-Benzenesulfonylamino-3-{3-[7-(3-benzyloxycarbonylamino-propoxy)-4-oxo-4H-quinolizin-3-yl]-ureido}-propionic acid tert-butyl ester (25 mg, 0.036 mmol) in dichloromethane (3 mL) was added TFA(3 ml) at room temperature. The reaction mixture was stirred overnight and then solvents were evaporated under reduced pressure. The residue was triturated with ether(2×5 ml) and dried. The resulting solid was purified by flash chromatography (10% methanol in ethyl acetate) to give 18 mg of compound VI which was characterized by 1HNMR (300 MHz) (CD3OD) δ: 8.56 (d, 1H, J=7 Hz), 8.40 (s, 1H), 7.92 (m, 2H), 7.42-7.60 (m, 4H), 7.25 (m, 5H), 6.91-7.04 (m, 2H), 5.12 (s, 2H), 4.19 (t, 2H), 3.63 (m, 1H), 3.50 (m, 2H), 3.20 (m, 2H), 2.02 (m, 2H)

Workup

  1. customsolvents were evaporated under reduced pressure
  2. customThe residue was triturated with ether(2×5 ml)
  3. customdried
  4. customThe resulting solid was purified by flash chromatography (10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-9a065cd5d03f4b87885fecefb8d273dc
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

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