Trifluoroacetic acid → HCID 14463815, compound

HRID 1607141Notes

Reaction equation

C(OC([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]1=[O:22])=O)(C)(C)C.[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26]>>[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].[NH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]1=[O:22]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 11748781HCID 11748781, compound

Product 1

HCID 14463815HCID 14463815, compoundYield 100%

Procedure

(3R)-3-t-Butoxycarbonylamino-1-benzyloxypyrrolidin-2-one (Example 1(c), 19.02 g, 62.2 mmol) was dissolved in trifluoracetic acid (150 ml). After 15 mins the solution was evaporated and the residue was crystallised from diethyl ether to give the title compound (20.31 g, 100%). mp=185° C. [α]D =+41.4° (c=1% MeOH), 1H NMR δ (D2O) 7.52-7.48 (5H, m, phenyl), 5.04 (2H, s, OCH2), 4.13 (1H, t, J=9.26 Hz, αCH--CH2), 3.63-3.59 (2H, m, CH2 --N), 2.61-2.57 (1H, m, --CH--CHA --HB), 2.13-2.02 (1H, m, --CH--CHAHB). m/e (FAB+) 207 (M+1); (FAB-) 205 (M-1).

Workup

customAfter 15 mins the solution was evaporated
customthe residue was crystallised from diethyl ether

Sources & evidence

ORD record: ord-5927d6686cb74675ad35669e5d452541
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863953

Reaction notes

Loading…