Acetic Acid → HCID 67330851, compound

HRID 409998Notes

Reaction equation

HRID 409998 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[C:8](O)(=O)C.[BH4-].[Na+].[CH3:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([CH:31]=1)[C:20]([NH:22][CH:23]1[CH:30]2[CH:26]([NH:27][CH2:28][CH2:29]2)[CH2:25][CH2:24]1)=[O:21].[CH3:32][N:33](C)C=O>>[CH:6]([N:3]1[CH:4]=[C:5]([N:27]2[CH2:28][CH2:29][CH:30]3[CH:23]([NH:22][C:20](=[O:21])[C:19]4[CH:31]=[C:15]([CH3:14])[CH:16]=[N:17][CH:18]=4)[CH2:24][CH2:25][CH:26]23)[CH:32]=[N:33]1)([CH3:7])[CH3:8]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 67369003HCID 67369003, compound

Product 1

HCID 67330851HCID 67330851, compound

Procedure

A 5 mL vial was charged with a magnetic stirbar, the aromatic aldehyde (0.1 mmol), dimethylformamide (1.5 mL) and triethylamine (0.3 mmol). The mixture was allowed to stir for 10 min at room temperature. Acetic acid (0.75 mmol) and sodium borohydride (0.15 mmol) were then added and allowed to stir for 5 min prior to addition of Compound 13 (0.1 mmol). The product was purified by mass-directed column chromatography. LC-MS, M+1=368.3

Workup

  1. additionA 5 mL vial was charged with a magnetic stirbar
  2. stirringto stir for 5 min
  3. customThe product was purified by mass-directed column chromatography

Sources & evidence

ORD record
ord-f3a54873194549f0bd3e225411cf2e08
Source dataset
uspto-grants-2014_06
Patent number
US08759539B2

Reaction notes

Loading…