Acetic Anhydride → HCID 16737182, compound

HRID 913201Notes

Reaction equation

HRID 913201 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[CH2:9][C@H:8]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][C@H:6]1[C:19]([OH:21])=[O:20])=[O:4].C(N(CC)CC)C.[C:29](OC(=O)C)(=[O:31])[CH3:30]>CC(C)=O>[C:29]([NH:1][CH2:2][C:3]([N:5]1[CH2:9][C@H:8]([NH:10][C:11](=[O:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:7][C@H:6]1[C:19]([OH:21])=[O:20])=[O:4])(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 16656685Danegaptide

Product 1

HCID 16737182HCID 16737182, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (2S4R)1-(2-Amino-acetyl)-4-benzoylamino-pyrrolidine-2-carboxylic acid (0.05 g, 0.17 mmol) and triethylamine (Aldrich) (0.19 mL, 1.37 mmol, 8 equivalents) in acetone (3 mL) was slowly added acetic anhydride (0.13 mL, 1.37 mmol, 8 equivalents) with stirring at room temperature under nitrogen atmosphere. The mixture was stirred for 3 hours while monitored by LCMS. Upon completion, the volatiles were removed in vacuo and the residue was purified by preparative HPLC (column: Xterra MSC18 50×250 mm, 10 u) using 40/60 to 90/10 methanol/water gradient (0.1% formic acid in methanol and 0.1 formic acid in water) to afford 0.020 g (35% yield) of the desired product as white solid with limited solubility in organic solvents.

Workup

  1. stirringThe mixture was stirred for 3 hours
  2. customUpon completion, the volatiles were removed in vacuo
  3. customthe residue was purified by preparative HPLC (column: Xterra MSC18 50×250 mm, 10 u)

Sources & evidence

ORD record
ord-0abd8966c1034404a1f2f24f02ebc51f
Source dataset
uspto-grants-2011_09
Patent number
US08026272B2

Reaction notes

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