Trifluoroacetic acid → HCID 178453525, compound

HRID 1802080Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][C@H:23]3[CH2:28][CH2:27][C@H:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:25][CH2:24]3)[CH:18]=2)[N:13]=1)([CH3:11])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].NC(C1C=CC2C(=CC=C(O[C@H]3CC[C@H](C(C)(C)C)CC3)C=2[C:49]([F:52])([F:51])[F:50])N=1)(C)CO.C(O)(C(F)(F)F)=O>>[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][C@H:23]3[CH2:28][CH2:27][C@H:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:25][CH2:24]3)[C:18]=2[C:49]([F:52])([F:51])[F:50])[N:13]=1)([CH3:11])[CH2:9][OH:10])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 178453527HCID 178453527, compound

HCID 178464711HCID 178464711, compound

Product 1

HCID 178453525HCID 178453525, compoundYield 95%

Procedure

{1-[6-(trans-4-tert-Butyl-cyclohexyloxy)-5-trifluoromethyl-quinolin-2-yl]-2-hydroxy-1-methyl-ethyl}-carbamic acid tert-butyl ester Enantiomer 1 was synthesized as per {1-[6-(trans-4-tert-Butyl-cyclohexyloxy)-quinolin-2-yl]-2-hydroxy-1-methyl-ethyl}-carbamic acid tert-butyl ester Enantiomer 1 (Example 28) in 95% yield using 2-amino-2-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-quinolin-2-yl]-propan-1-ol Enantiomer 1 as starting material (bis-TFA salt).

Sources & evidence

ORD record: ord-61487a9bd0f84cc3aa0b06b9f28fb0ad
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349849B2

Reaction notes

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