Propanal → HCID 22325513, compound

HRID 496315Notes

Reaction equation

HRID 496315 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([C:12]3[CH:17]=[C:16]([S:18]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)(=[O:20])=[O:19])[CH:15]=[CH:14][C:13]=3[O:27][CH2:28][CH2:29][CH3:30])[NH:11][C:5]=2[N:4]([CH2:31][CH2:32][CH3:33])[C:3]1=[O:34].[CH:35](=O)[CH2:36][CH3:37].[Na]>CO.C(O)(=O)C>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([C:12]3[CH:17]=[C:16]([S:18]([N:21]4[CH2:26][CH2:25][N:24]([CH2:35][CH2:36][CH3:37])[CH2:23][CH2:22]4)(=[O:20])=[O:19])[CH:15]=[CH:14][C:13]=3[O:27][CH2:28][CH2:29][CH3:30])[NH:11][C:5]=2[N:4]([CH2:31][CH2:32][CH3:33])[C:3]1=[O:34]

Participants

6

Reactant 3

HCID 527PropanalHCID 5360545SodiumHCID 22325564HCID 22325564, compound

Product 1

HCID 22325513HCID 22325513, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of the title compound of example 87 (50 mg, 0.1 mmol), propanal (0.073 mL, 1 mmol) and 3 Å molecular sieves (300 mg) in methanol (2 mL) and acetic acid (0.1 mL), was stirred at room temperature for 4 hours. Then sodium cianoborohydride (32 mg, 0.51 mmol) was slowly added and the mixture was stirred at room temperature overnight. The reaction mixture was purified by solid phase extraction using a Varian Bond Elut SCX cartridge (methanol for washing, methanol-ammonia for elution) to yield the title compound (40 mg, 72%).

Workup

  1. customThe reaction mixture was purified by solid phase extraction
  2. washa Varian Bond Elut SCX cartridge (methanol for washing, methanol-ammonia for elution)

Sources & evidence

ORD record
ord-cb3343eb914f4ffeaf9224f01625000c
Source dataset
uspto-grants-2005_09
Patent number
US06943253B2

Reaction notes

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