Trifluoroacetic acid → HCID 58010039, compound

HRID 1854433Notes

Reaction equation

HRID 1854433 reaction equation
C(OC([N:8]([C:35]1[N:36]=[C:37]2[CH:43]=[CH:42][N:41]([S:44]([C:47]3[CH:53]=[CH:52][C:50]([CH3:51])=[CH:49][CH:48]=3)(=[O:46])=[O:45])[C:38]2=[N:39][CH:40]=1)[CH2:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH2:21][CH:22]2[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])[CH2:13]1)=O)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>>[S:44]([N:41]1[C:38]2[N:39]=[CH:40][C:35]3[N:36]([C:10]([C@@H:12]4[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH2:21][CH:22]5[C:23]6[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=6[C:29]6[C:34]5=[CH:33][CH:32]=[CH:31][CH:30]=6)=[O:19])[CH2:13]4)=[CH:9][N:8]=3)[C:37]=2[CH:43]=[CH:42]1)([C:47]1[CH:53]=[CH:52][C:50]([CH3:51])=[CH:49][CH:48]=1)(=[O:45])=[O:46]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 58010029HCID 58010029, compound

Product 1

HCID 58010039HCID 58010039, compoundYield 101.9%

Conditions

Temperature
25 °C

Procedure

A mixture of (R)-(9H-fluoren-9-yl)methyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)piperidine-1-carboxylate (0.20 g, 0.27 mmol), TFA (1.0 mL, 13 mmol) and TFAA (1.0 mL, 7.1 mmol) was stirred at about 25° C. for about 16 h. The reaction mixture was partitioned between EtOAc (50 mL) and aqueous saturated NaHCO3 (2×50 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give (R)-(9H-fluoren-9-yl)methyl 3-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)piperidine-1-carboxylate as a clear oil (0.17 g, 99%): LC/MS (Table 2, Method a) Rt=2.68 min; MS m/z: 618 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between EtOAc (50 mL) and aqueous saturated NaHCO3 (2×50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c720766ccc341a3885e47b9b19ce205
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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