Trifluoroacetic acid methylene chloride → HCID 10343596, compound

HRID 264905Notes

Reaction equation

FC(F)(F)C(O)=O.ClCCl.[CH2:11]([NH:15][C:16](=[O:49])[C@H:17]([CH3:48])[CH2:18][C@H:19]([OH:47])[C@@H:20]([NH:39]C(OC(C)(C)C)=O)[CH2:21][C@@H:22]([CH:36]([CH3:38])[CH3:37])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:33][C:34]#[N:35])[CH:25]=1)[CH2:12][CH2:13][CH3:14]>ClCCl>[CH2:11]([NH:15][C:16](=[O:49])[C@H:17]([CH3:48])[CH2:18][C@H:19]([OH:47])[C@@H:20]([NH2:39])[CH2:21][C@@H:22]([CH:36]([CH3:37])[CH3:38])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:33][C:34]#[N:35])[CH:25]=1)[CH2:12][CH2:13][CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

1.5 ml of a mixture of trifluoroacetic acid/dichloromethane=1:3 are added at 0° C., with stirring, to a solution of 35 mg of N-tert-butoxycarbonyl-2(R)-methyl-4(S)-hydroxy-5(S)-amino-7(S)-isopropyl-8-(3-cyanomethoxy-4-methoxy-phenyl)-octanoic acid (N-butyl)-amide in 1 ml of dichloromethane, and the mixture is stirred for a further 3 hours at 0° C. and then concentrated by evaporation. The residue is purified by FC (5 g of silica gel, dichloromethane/methanol=9:1). This yields the title compound: Rf (dichloromethane/methanol=9:1)=0.19; Rt (I)=19.59 minutes; FAB-MS(M+H)+ =448.

Workup

concentrationconcentrated by evaporation
customThe residue is purified by FC (5 g of silica gel, dichloromethane/methanol=9:1)

Sources & evidence

ORD record: ord-e8861672314d4c10bbb33b16c03a7eb5
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646143

Reaction notes

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