Triethylamine → HCID 16079061, compound

HRID 1692634Notes

Reaction equation

HRID 1692634 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]([O:10][C:11]3[C:12]([CH3:23])=[C:13]([O:21][CH3:22])[CH:14]=C(C(O)=O)C=3[O:17][C:6]=2[C:5]([CH:24]=[O:25])=[C:4]([OH:26])[CH:3]=1)=[O:9].CCN=C=N[CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36].C1C=CC2N([OH:47])N=NC=2C=1.Cl.CNC.C(N(CC)CC)C>CN(C=O)C.O>[CH3:37][N:35]([CH3:36])[C:34]([C:33]1[C:32]2[O:17][C:6]3[C:5]([CH:24]=[O:25])=[C:4]([OH:26])[CH:3]=[C:2]([CH3:1])[C:7]=3[C:8](=[O:9])[O:10][C:11]=2[C:12]([CH3:23])=[C:13]([O:21][CH3:22])[CH:14]=1)=[O:47]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 23725Psoromic AcidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 16079061HCID 16079061, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Psoromic acid (35 mg, 1 mmol), EDCI (20 mg, 1.5 mmol) and HOBt (23 mg, 1.5 mmol) were added into DMF (5 ml) under ice bath. The solution was stirred for half an hour, and then to the reaction mixture was added dropwise a solution of dimethyl-amine hydrochloride (8.7 mg, 1 mmol) and triethylamine (0.014 ml, 1 mmol) in anhydrous DMF (3 ml). The reaction was monitored by TLC. Upon completion, the reaction mixture was poured into 60 mL of water and extracted with ethyl acetate. The organic layer was subsequently washed with saturated NaHCO3, saturated brine, dried over anhydrous MgSO4, filtered, evaporated by a rotatory evaporator, and purified by column chromatography to give a white solid product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was subsequently washed with saturated NaHCO3, saturated brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated by a rotatory evaporator
  6. custompurified by column chromatography
  7. customto give a white solid product

Sources & evidence

ORD record
ord-67608dec15514567a967fea98b03bbea
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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