Trifluoroacetic acid → HCID 9821989, compound

HRID 987225Notes

Reaction equation

HRID 987225 reaction equation
C(OC([NH:8][CH2:9][CH2:10][NH:11][C:12]1[CH:13]=[CH:14][N:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([C:22]([NH:24][CH:25]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:26][C:27]([OH:29])=[O:28])=[O:23])[C:16]2=[O:36])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][CH2:10][NH:11][C:12]1[CH:13]=[CH:14][N:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([C:22]([NH:24][CH:25]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:26][C:27]([OH:29])=[O:28])=[O:23])[C:16]2=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 56616963HCID 56616963, compound

Product 1

HCID 9821989HCID 9821989, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (+/−)-3-{[8-(2-tert-butoxycarbonylamino-ethylamino)-4-oxo-4H-quinolizine-3-carbonyl]-amino}-3-phenyl-propionic acid (20.5 mg, 0.042 mmol) in dichloromethane (1 ml) at room temperature was added trifluoroacetic acid (1 ml). The resulting mixture was stirred at room temperature for 45 min. The solvent was removed under vacuum and the resulting residue was subjected to a silica gel chromatography (EtOH:H2O: NH4OH, 90:5:5) to give desired product which was further lyophilized to afford a yellowish solid (30 mg, 73%) which was characterized by 1HNMR (400 MHz, D2O) δ: 2.58-2.65 (m, 2H), 2.90-3.10 (m, 2H), 3.15-3.25 (m, 2H), 5.21 (m, 1H), 6.0-8.7 (m, 10H).

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-c0d7f3d70a8c48e2a554df7765e720db
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

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