Trifluoroacetic acid → HCID 71060560, compound

HRID 1036691Notes

Reaction equation

C(OC(=O)[NH:7][C:8]([C:11](=[O:44])[NH:12][C@H:13]([CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)[C:14]([N:16]1[CH2:33][CH2:32][CH2:31][C:18]2([C:22](=[O:23])[N:21]([CH3:24])[CH2:20][CH:19]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17]1)=[O:15])([CH3:10])[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]([CH3:10])([CH3:9])[C:11]([NH:12][C@H:13]([CH2:34][O:35][CH2:36][C:37]1[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=1)[C:14]([N:16]1[CH2:33][CH2:32][CH2:31][C:18]2([C:22](=[O:23])[N:21]([CH3:24])[CH2:20][CH:19]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17]1)=[O:15])=[O:44]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of {1-[(R)-1-(4-Fluoro-benzyloxymethyl)-2-(2-methyl-1-oxo-4-phenyl-2,7-diaza-spiro[4.5]dec-7-yl)-2-oxo-ethylcarbamoyl]-1-methyl-ethyl}-carbamic acid tert-butyl ester (Intermediate from step 3) (154 mg, 0.24 mmol) in DCM (2.5 ml) was cooled with an ice bath and TFA (0.57 ml, 7.4 mmol) was added. The resulting solution was stirred for 3 h at 0° C. The reaction mixture was diluted with DCM (20 ml) and quenched at 0° C. with 2M NaOH aqueous solution (10 ml). The organic phase was separated, washed with brine (5 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 0-2.5% MeOH in DCM to afford the title compound.

Workup

customquenched at 0° C. with 2M NaOH aqueous solution (10 ml)
customThe organic phase was separated
washwashed with brine (5 ml)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica eluting with 0-2.5% MeOH in DCM

Sources & evidence

ORD record: ord-07ca2d3379584a87ada49abfd038d69a
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546416B2

Reaction notes

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