2-Amino-4,4,4-trifluorobutanoic acid → HCID 58293478, compound

HRID 1627128Notes

Reaction equation

HRID 1627128 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][CH:16]([CH2:20][C:21]([F:24])([F:23])[F:22])[C:17]([OH:19])=[O:18].[CH:25]([C:27]1[CH:32]=[CH:31][N:30]=[C:29]2[N:33]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH:34]=[C:35]([C:36]([O:38][CH3:39])=[O:37])[C:28]=12)=O>C(Cl)Cl>[C:43]([O:42][C:40]([N:33]1[C:29]2=[N:30][CH:31]=[CH:32][C:27]([CH2:25][NH:15][C@H:16]([CH2:20][C:21]([F:24])([F:23])[F:22])[C:17]([OH:19])=[O:18])=[C:28]2[C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34]1)=[O:41])([CH3:46])([CH3:45])[CH3:44]

Participants

5

Reactant 3

HCID 3530832-Amino-4,4,4-trifluorobutanoic acidHCID 5049666Sodium triacetoxyborohydrideHCID 497616131-tert-Butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate

Product 1

HCID 58293478HCID 58293478, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 10 mL round bottom flask was added sodium triacetoxyborohydride (104 mg, 0.493 mmol), 2-amino-4,4,4-trifluorobutanoic acid (51.6 mg, 0.329 mmol) and DCM (2 mL). The reaction mixture was stirred for 30 min after which was added 1-tert-butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate (50 mg, 0.164 mmol) in DCM (2 mL). The reaction was stirred at room temperature for 2 h and then quenched with MeOH (3 drops). The mixture was concentrated to afford the title compound, which was used in the next step without further purification. [M+H] calc'd for C19H22F3N3O6, 446; found, 446.5.

Workup

  1. stirringThe reaction was stirred at room temperature for 2 h
  2. customquenched with MeOH (3 drops)
  3. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-6553fe5b415740639d609170dd4e4b7a
Source dataset
uspto-grants-2014_07
Patent number
US08785429B2

Reaction notes

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