1,3-Propanediol → HCID 67423120, compound

HRID 1393027Notes

Reaction equation

HRID 1393027 reaction equation
[CH3:1][N:2]([CH:6]1[CH2:19][C:18]2[C:9]([CH3:28])([CH:10]3[CH:15]([CH2:16][CH:17]=2)[CH:14]2[CH2:20][CH2:21][CH:22]4[CH:23]([CH3:27])[N:24]([CH3:26])[CH2:25][C:13]24[CH2:12][CH2:11]3)[CH2:8][CH2:7]1)[C:3](Cl)=[O:4].[CH2:29]([OH:33])[CH2:30][CH2:31][OH:32]>N1C=CC=CC=1>[OH:32][CH2:31][CH2:30][CH2:29][O:33][C:3](=[O:4])[N:2]([CH3:1])[CH:6]1[CH2:19][C:18]2[C:9]([CH3:28])([CH:10]3[CH:15]([CH2:16][CH:17]=2)[CH:14]2[CH2:20][CH2:21][CH:22]4[CH:23]([CH3:27])[N:24]([CH3:26])[CH2:25][C:13]24[CH2:12][CH2:11]3)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 104421,3-PropanediolHCID 72355931HCID 72355931, compound

Product 1

HCID 67423120HCID 67423120, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Compound 189A (30 mg, 0.074 mmol) and 1,3-propanediol (54μL, 0.061 mmol), were dissolved in pyridine (1 mL). The mixture was stirred at room temperature for 5 days. Stripped of pyridine, the crude reaction mixture was purified on silica gel column using 0.5% ammonium hydroxide and 5% methanol in dichloromethane to give the desired product (7.3 mg, 22.8% yield).

Workup

  1. customwas purified on silica gel column

Sources & evidence

ORD record
ord-0c044b8a367a4e86bde704e0f5436a1f
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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