Trifluoroacetic acid → HCID 86759200, compound

HRID 987220Notes

Reaction equation

HRID 987220 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]([C:12]1[CH:13]=[C:14]2[N:19]([C:20](=[O:22])[CH:21]=1)[CH:18]=[C:17]([CH2:23][NH:24]C(OC(C)(C)C)=O)[CH:16]=[CH:15]2)=[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].[NH2:24][CH2:23][C:17]1[CH:16]=[CH:15][C:14]2[N:19]([C:20](=[O:22])[CH:21]=[C:12]([C:10]([NH:9][CH2:8][CH:7]([NH:32][S:33]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)(=[O:34])=[O:35])[C:6]([OH:42])=[O:5])=[O:11])[CH:13]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 56627145HCID 56627145, compound

Product 1

HCID 86759200HCID 86759200, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-Benzenesulfonylamino-3-{[7-(tert-butoxycarbonylamino-methyl)-4-oxo-4H-quinolizine-2-carbonyl]-amino}-propionic acid tert-butyl ester (21.2 mg, 0.035 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (2 mL). The mixture was stirred overnight, evaporated to dryness and triturated in ether (3×) and dichloromethane (1×). The solid was dried and characterized to yield 62% (10 mg, 0.022 mmol) of the title compound which was characterized by 1HNMR (400 MHz, CD3OD) δ: 9.03 (s, 1H), 7.93-7.83 (m, 3H), 7.64 (dd, 1H, J=9, 1.5 Hz), 7.55-7.45 (m, 3H), 7.26 (s, 1H), 6.92 (d, 1H, J=1.5 Hz), 4.29 (s, 2H), 4.22 (dd, 1H, J=7.5, 5 Hz), 3.81-3.77 (dd, 1H, J=13.5, 5 Hz), 3.55-3.45 (m, 1H).

Workup

  1. customevaporated to dryness
  2. customtriturated in ether (3×)
  3. customThe solid was dried

Sources & evidence

ORD record
ord-5d5e69c646d640ce89aa61d0f4d97479
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

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