Trifluoroacetic acid → HCID 68079993, compound

HRID 1508577Notes

Reaction equation

HRID 1508577 reaction equation
[N:1]1([C:5]2[N:10]=[C:9]([CH2:11][N:12]3[C@@H:16]([CH3:17])[C@@H:15]([C:18]4[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=4)[O:14][C:13]3=[O:26])[C:8]([C:27]3[CH:28]=[C:29]([CH2:35][CH2:36][C:37]([OH:39])=O)[CH:30]=[CH:31][C:32]=3[O:33][CH3:34])=[CH:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[OH-].[NH4+:47].C(O)(C(F)(F)F)=O>C(Cl)Cl.CN(C=O)C>[N:1]1([C:5]2[N:10]=[C:9]([CH2:11][N:12]3[C@@H:16]([CH3:17])[C@@H:15]([C:18]4[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=4)[O:14][C:13]3=[O:26])[C:8]([C:27]3[CH:28]=[C:29]([CH2:35][CH2:36][C:37]([NH2:47])=[O:39])[CH:30]=[CH:31][C:32]=3[O:33][CH3:34])=[CH:7][CH:6]=2)[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 68083524HCID 68083524, compound

Product 1

HCID 68079993HCID 68079993, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-(6-azetidin-1-yl-2-{[(4S,5R)-5-(3,5-dimethylphenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}pyridin-3-yl)-4-methoxyphenyl]propanoic acid (EXAMPLE 228) (8 mg, 0.014 mmol) in DCM (2 ml) was added oxalyl chloride (2M in DCM) (100 μl, 0.200 mmol) and a drop of DMF. The solution was stirred for 30 minutes, concentrated, dissolved in THF (2 ml), added ammonium hydroxide (50 μl, 0.360 mmol) and stirred overnight. The mixture was acidified with 50 μl of TFA, concentrated, dissolved in MeOH, filtered, and purified by RP HPLC to afford the title compound. Mass spectrum (ESI) 529.5. 1H NMR (500 MHz, CD3OD): δ 7.31 (d, J=8.3 Hz, 1H); 7.20 (dd, J=8.4, 2.3 Hz, 1H); 7.02 (s, 1H); 6.96 (s, 2H); 6.83 (s, 2H); 6.35 (d, J=8.4 Hz, 1H); 5.40 (d, J=8.5 Hz, 1H); 4.80-4.48 (m, 1H); 4.24-3.64 (m, 2H); 4.05 (t, J=7.4 Hz, 4H); 3.75 (s, 3H); 2.88 (m, 2H); 2.48 (m, 3H); 2.41 (m, 2H); 2.28 (s, 6H); 0.59 (m, 3H).

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in THF (2 ml)
  3. stirringstirred overnight
  4. concentrationconcentrated
  5. dissolutiondissolved in MeOH
  6. filtrationfiltered
  7. custompurified by RP HPLC

Sources & evidence

ORD record
ord-06a6bcb58242475887455684fdd563e0
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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