1,2-Dichloroethane → HCID 67076595, compound

HRID 521470Notes

Reaction equation

HRID 521470 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([NH2:24])[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[C:26]1([CH2:32][C:33](O)=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([NH:24][C:33](=[O:34])[CH2:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:17]=2)[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13]1)=[O:4]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 999Phenylacetic AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 67076603HCID 67076603, compound

Product 1

HCID 67076595HCID 67076595, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The compound of step 2 (0.042 g, 0.12 mmol) and phenylacetic acid (0.013 g, 0.092 mmol) were dissolved in DCM (3 ml) and DMF (1 ml), NMM (0.031 ml, 0.28 mmol), HOBT (0.016 g, 0.12 mmol) and EDC (0.021 g, 0.12 mmol) were added, and the mixture was stirred overnight. LC/MS analysis showed complete conversion. The mixture was filtered, the filtrate subjected to preparative RP HPLC (water/ACN gradient), and the fractions containing the title compound freeze-dried. Yield: 0.042 g.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe fractions containing the title compound
  3. customfreeze-dried

Sources & evidence

ORD record
ord-8362037f57f04c6395b4153c1c68627b
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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