D-Cyclopropylglycine → HCID 58293548, compound

HRID 1968218Notes

Reaction equation

HRID 1968218 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@H:16]([CH:20]1[CH2:22][CH2:21]1)[C:17]([OH:19])=[O:18].[CH:23]([C:25]1[CH:30]=[CH:29][N:28]=[C:27]2[N:31]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:32]=[C:33]([C:34]([O:36][CH3:37])=[O:35])[C:26]=12)=O>C(Cl)Cl>[C:41]([O:40][C:38]([N:31]1[C:27]2=[N:28][CH:29]=[CH:30][C:25]([CH2:23][NH:15][C@H:16]([CH:20]3[CH2:22][CH2:21]3)[C:17]([OH:19])=[O:18])=[C:26]2[C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32]1)=[O:39])([CH3:44])([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 1520863D-CyclopropylglycineHCID 5049666Sodium triacetoxyborohydrideHCID 497616131-tert-Butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate

Product 1

HCID 58293548HCID 58293548, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 10 mL round bottom flask was added sodium triacetoxyborohydride (104 mg, 0.493 mmol), (R)-2-amino-2-cyclopropylacetic acid (37.8 mg, 0.329 mmol), and DCM (2 mL). The reaction mixture was stirred at room temperature in 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 C20H25N3O6, 404; found, 404.3.

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-ec5add6c3e7e4cf893091a9d73c9f823
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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