Trifluoroacetic acid → HCID 54565765, compound

HRID 483861Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:46])[C@H:10]([CH3:45])[NH:11][C:12](=[O:44])[C@H:13]([CH2:40][CH:41]([CH3:43])[CH3:42])[N:14]([C:16](=[O:39])[C@H:17]([CH:35]([CH2:37][F:38])[CH3:36])[NH:18][C:19](=[O:34])[C@H:20]([CH2:30][CH:31]([CH3:33])[CH3:32])[N:21](C(OC(C)(C)C)=O)[CH3:22])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:46])[C@H:10]([CH3:45])[NH:11][C:12](=[O:44])[C@H:13]([CH2:40][CH:41]([CH3:43])[CH3:42])[N:14]([C:16](=[O:39])[C@H:17]([CH:35]([CH2:37][F:38])[CH3:36])[NH:18][C:19](=[O:34])[C@H:20]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH:21][CH3:22])[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -15 °C

Procedure

To a stirred solution of 650 mg (0.001 mole) of Boc-N-methyl-L-leucyl-4-fluoro-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester in 10 ml of dry methylene chloride and cooled at 10° C. was added 6.5 ml of trifluoroacetic acid, which was previously cooled at -15° C. The reaction was stirred for 16 hours, then carefully poured into a mixture of 7.7 g. of sodium bicarbonate, ice, and 75 ml of methylene chloride with stirring. The organic layer was extracted with 3×20 ml of saturated sodium bicarbonate solution, then dried over magnesium sulfate. The solvent was removed in vacuo leaving the product as a stiff oil, which weighed 540 mg. The yield is 989% of theory and the FAB m.s. showed a molecular ion peak at 551.

Workup

additioncarefully poured into a mixture of 7.7 g
extractionThe organic layer was extracted with 3×20 ml of saturated sodium bicarbonate solution
dry with materialdried over magnesium sulfate
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-1b409d800a894708aae32d213b4a7890
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05227467

Reaction notes

Loading…