Pyridine → Trifluoroacetic acid

HRID 573464Notes

Reaction equation

HRID 573464 reaction equation
C(OC(=O)[NH:7][CH:8](C)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:41])[NH:17][CH:18]([CH:30]1[CH:37]2[CH2:38][CH:33]3[CH2:34][C:35]([OH:40])([CH2:39][CH:31]1[CH2:32]3)[CH2:36]2)[C:19]([N:21]1[CH2:26][CH:25]2[CH:23]([CH2:24]2)[CH:22]1[C:27](=O)[NH2:28])=[O:20])=[O:10])(C)(C)C.N1C=C[CH:47]=[CH:46][CH:45]=1.[F:50][C:51]([F:62])([F:61])[C:52]([O:54]C(=O)C(F)(F)F)=[O:53]>C1COCC1>[F:50][C:51]([F:62])([F:61])[C:52]([OH:54])=[O:53].[C:27]([CH:22]1[N:21]([C:19](=[O:20])[CH:18]([NH:17][C:16]([CH:12]2[CH2:13][CH2:14][CH2:15][N:11]2[C:9](=[O:10])[CH:8]([NH2:7])[CH:46]([CH3:47])[CH3:45])=[O:41])[CH:30]2[CH:31]3[CH2:32][CH:33]4[CH2:34][C:35]([OH:40])([CH2:36][CH:37]2[CH2:38]4)[CH2:39]3)[CH2:26][CH:25]2[CH:23]1[CH2:24]2)#[N:28]

Participants

6

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 67450722HCID 67450722, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 67449809HCID 67449809, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Analogously to example 23 the solution of 1.7 gm of (2-{2-[2-(2-Carbamoyl-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(5-hydroxy-adamantan-2-yl)-2-oxo-ethylcarbamoyl]-pyrrolidin-1-yl}-1-methyl-2-oxo-ethyl)-carbamic acid tert-butyl ester in THF was added into the mixture of pyridine (1.0 ml) and Trifluoro acetic anhydride (0.95 ml). The reaction mixture was stirred at room temperature. THF was evaporated and residue was taken into MeOH and 10 ml 10% K2CO3 solution was added. MeOH was evaporated and aq. layer was extracted with EtoAC. The combined EtoAC layers were washed with 1N HCl and aq. NaHCO3, dried over sodium sulphate and concentrated in vacuum to give crude product. The crude product was purified by column chromatography to get pure Trifluoro acetic acid salt of 1-(2-Amino-3-methyl-butyryl)-pyrrolidine-2-carboxylic acid [2-(2-cyano-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(5-hydroxy-adamantan-2-yl)-2-oxo-ethyl]-amide of formula 37. (Yield: 0.7 gm)

Workup

  1. customTHF was evaporated
  2. additionwas added
  3. customMeOH was evaporated
  4. extractionaq. layer was extracted with EtoAC
  5. washThe combined EtoAC layers were washed with 1N HCl and aq. NaHCO3
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuum
  8. customto give crude product
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e2bab41e1399401c91074adac732ec3d
Source dataset
uspto-grants-2015_05
Patent number
US09029567B2

Reaction notes

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