Acetic Acid → HCID 68998805, compound

HRID 1821377Notes

Reaction equation

HRID 1821377 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19]2)=[N:2]1.[CH2:25]([CH2:27][NH2:28])[OH:26].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[CH:22]=[CH:21][C:20]([CH2:23][NH:28][CH2:27][CH2:25][OH:26])=[CH:19]2)=[N:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 700EthanolamineHCID 5049666Sodium triacetoxyborohydrideHCID 86628206HCID 86628206, compound

Product 1

HCID 68998805HCID 68998805, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Compound 167 (0.06 g, 0.19 mmol) was dissolved in dichloroethane (2.0 mL) and the solution was added with ethanolamine (35 μL, 0.57 mmol), acetic acid (63 μL, 0.57 mmol) and sodium triacetoxyborohydride (0.12 g, 0.57 mmol), followed by stirring at room temperature for 1 hour. The reaction mixture was added with water, extracted with ethyl acetate and the organic layer was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/methanol=9/1) to obtain Compound 187 (24 mg, 35%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationthe organic layer was concentrated
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol=9/1)

Sources & evidence

ORD record
ord-03f63200fdc14fcc85bfc211434a37f8
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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