Trifluoroacetic acid → HCID 69032709, compound

HRID 2416629Notes

Reaction equation

C(OC([NH:8][CH2:9][C:10]1[N:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:18]2=[C:25]3[CH2:34][N:33]4[C:28](=[CH:29][C:30]5[C@:39]([CH2:41][CH3:42])([OH:40])[C:38](=[O:43])[O:37][CH2:36][C:31]=5[C:32]4=[O:35])[C:26]3=[N:27][C:16]3[C:17]2=[C:12]([CH:13]=[CH:14][CH:15]=3)[N:11]=1)=O)(C)(C)C.[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47]>>[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47].[NH2:8][CH2:9][C:10]1[N:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:18]2=[C:25]3[CH2:34][N:33]4[C:28](=[CH:29][C:30]5[C@:39]([CH2:41][CH3:42])([OH:40])[C:38](=[O:43])[O:37][CH2:36][C:31]=5[C:32]4=[O:35])[C:26]3=[N:27][C:16]3[C:17]2=[C:12]([CH:13]=[CH:14][CH:15]=3)[N:11]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 69034165HCID 69034165, compound

Product 1

HCID 69032709HCID 69032709, compoundYield 80%

Procedure

(9S)-2-(t-Butoxycarbonylamino)methyl-9-ethyl-9-hydroxy-1-pentyl-1H,12H-pyrano[3″,4″:6′,7′]indolizino[1′,2′:6,5]pyrido[4,3,2-de]quinazoline-10,13(9H,15H)-dione (33 mg, 0.056 mmol) was dissolved in trifluoroacetic acid (1 ml) and mixture was stirred for 1 hr. at room temperature. The solution was concentrated under reduced pressure and the resulting residue was purified by reverse-phase C-18 column chromatography to obtain pure product (27 mg, 80%).

Workup

customat room temperature
concentrationThe solution was concentrated under reduced pressure
customthe resulting residue was purified by reverse-phase C-18 column chromatography

Sources & evidence

ORD record: ord-deaae890aead4818b2dd5e25b0eb3ac2
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825194B2

Reaction notes

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