Trifluoroacetic acid → HCID 12149997, compound

HRID 1275046Notes

Reaction equation

C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(=O)[NH:22][CH2:23][C@H:24]([C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([C:35]([CH3:46])([CH3:45])[C:36]([N:38]3[CH:42]4[CH2:43][CH2:44][CH:39]3[CH2:40][CH2:41]4)=[O:37])[CH:33]=2)[NH:28][C:27]=1[C:47]1[CH:52]=[C:51]([CH3:53])[CH:50]=[C:49]([CH3:54])[CH:48]=1)[CH3:25])(C)(C)C>>[NH2:22][CH2:23][C@H:24]([C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([C:35]([CH3:46])([CH3:45])[C:36]([N:38]3[CH:42]4[CH2:43][CH2:44][CH:39]3[CH2:40][CH2:41]4)=[O:37])[CH:33]=2)[NH:28][C:27]=1[C:47]1[CH:52]=[C:51]([CH3:53])[CH:50]=[C:49]([CH3:54])[CH:48]=1)[CH3:25]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 53941834HCID 53941834, compound

Product 1

HCID 12149997HCID 12149997, compoundYield 99%

Conditions

Temperature: 0 °C

Procedure

To a solution of (S)-{2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-propyl}-carbamic acid tert-butyl ester (2.6 g in 90 mL methylene chloride) at 0° C. was added 5.2 mL anisole followed by 37 mL trifluoroacetic acid and the mixture stirred at 0° C. After 2 hours, the mixture was concentrated in vacuo and the residual acid removed by azeotrope with toluene. Purification by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:7:1) gave the title compound (2.1 g).

Workup

concentrationthe mixture was concentrated in vacuo
customthe residual acid removed by azeotrope with toluene
customPurification by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:7:1)

Sources & evidence

ORD record: ord-c6364282c6fe4db88c5c09cd41bebb8f
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06159975

Reaction notes

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