Trifluoroacetic acid → HCID 86599484, compound

HRID 855051Notes

Reaction equation

C(OC([NH:8][C:9]1[CH:34]=[CH:33][C:12]([CH2:13][C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:28]([O:30]CC)=[O:29])[CH:20]([C:24]([F:27])([F:26])[F:25])[O:21]3)=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36].[OH-].[Na+]>Cl.C1COCC1.O.C1COCC1.CO>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[NH2:8][C:9]1[CH:34]=[CH:33][C:12]([CH2:13][C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:28]([OH:30])=[O:29])[CH:20]([C:24]([F:27])([F:25])[F:26])[O:21]3)=[CH:16][CH:15]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

The ester from Step 1 was dissolved in 0.3 mL HCl in THF/H2O=1/1. The mixture was stirred at r.t for 2 days. Additional 2 mL TFA was added to above solution and the solution was stirred for 2 days. LCMS indicated that there was less than 10% product. The mixture was heated at 50° C. for 4 hrs. After purification, the combined deBoc-ester was redissolved in THF/MeOH=2/1 and NaOH (2.5 N, 2.5 eq). The mixture was stirred at r.t overnight. The mixture was purified by RPHPLC to give the title compound as an amorphous solid: ESHRMS m/z 350.0994 (M+H, C18H15O3F3N, Calc'd 350.0999). 1H NMR (acetone-d6/300 MHz) 7.38 (m, 3H), 7.11 (d, 1H, J=8.4 Hz), 7.00 (d, 1H, J=8.1 Hz), 6.93 (s, 1H), 6.71 (d, 1H, J=8.1 Hz), 5.78 (q, 1H, J=7.2 Hz), 4.04 (s, 2H).

Workup

stirringthe solution was stirred for 2 days
customAfter purification
stirringThe mixture was stirred at r.t overnight
customThe mixture was purified by RPHPLC

Sources & evidence

ORD record: ord-9819464a648c4a8985974910f5fda427
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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