Sodium triacetoxyborohydride → HCID 58293507, compound

HRID 1968247Notes

Reaction equation

HRID 1968247 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C@H:16]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].[Cl:31][C:32]1[C:33]([CH:54]=O)=[C:34]2[C:40]([C:41]([OH:43])=[O:42])=[CH:39][N:38]([S:44]([C:47]3[CH:53]=[CH:52][C:50]([CH3:51])=[CH:49][CH:48]=3)(=[O:46])=[O:45])[C:35]2=[N:36][CH:37]=1>C(Cl)Cl>[CH2:20]([O:19][C:17](=[O:18])[C@H:16]([NH:15][CH2:54][C:33]1[C:32]([Cl:31])=[CH:37][N:36]=[C:35]2[N:38]([S:44]([C:47]3[CH:53]=[CH:52][C:50]([CH3:51])=[CH:49][CH:48]=3)(=[O:46])=[O:45])[CH:39]=[C:40]([C:41]([OH:43])=[O:42])[C:34]=12)[C:27]([CH3:30])([CH3:29])[CH3:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 582934935-chloro-4-formyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acidHCID 58293508HCID 58293508, compound

Product 1

HCID 58293507HCID 58293507, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 10 mL round bottom flask was added sodium triacetoxyborohydride (86 mg, 0.407 mmol), (R)-benzyl 2-amino-3,3-dimethylbutanoate (130 mg, 0.407 mmol) and DCM (2 mL). The mixture was stirred at room temperature for 10 min and then cooled to 0° C. 5-Chloro-4-formyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (130 mg, 0.271 mmol) was added and the reaction mixture was stirred at 0° C. for 20 min to afford the title compound. [M+H] calc'd for C29H30ClN3O6S, 584; found, 584.0.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe reaction mixture was stirred at 0° C. for 20 min

Sources & evidence

ORD record
ord-e74beadf166247138b3c23698f4a46f1
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

Loading…