Acetic Acid → HCID 22714146, compound

HRID 352249Notes

Reaction equation

HRID 352249 reaction equation
[NH2:1][C:2]1[C:3]2[C:4]3[C:5](=[C:29]([CH3:32])[O:30][N:31]=3)[C:6](=[O:28])[N:7]([CH:12]3[CH2:17][CH2:16][CH2:15][CH:14]([CH2:18][NH:19][C:20](=[O:27])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:13]3)[C:8]=2[CH:9]=[CH:10][CH:11]=1.[CH3:33][C:34](O)=[O:35].CCN=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:34]([NH:1][C:2]1[C:3]2[C:4]3[C:5](=[C:29]([CH3:32])[O:30][N:31]=3)[C:6](=[O:28])[N:7]([CH:12]3[CH2:17][CH2:16][CH2:15][CH:14]([CH2:18][NH:19][C:20](=[O:27])[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:13]3)[C:8]=2[CH:9]=[CH:10][CH:11]=1)(=[O:35])[CH3:33]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22713909HCID 22713909, compound

Product 1

HCID 22714146HCID 22714146, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of a compound from Example 667 (0.025 g, 0.06 mmol) and AcOH (0.02 mL, 0.36 mmol) in DMF (1 mL) under N2 was added EDCI (0.023 g, 0.12 mmol) and DMAP (0.002 g, 0.01 mmol). The solution was stirred overnight, diluted with EtOAc, washed (H2O then brine), dried (MgSO4), filtered, and concentrated. Flash chromatography (silica gel, acetone/CH2Cl2 gradient) gave the title compound (0.023 g, 82%). Mass Spectrum (ES+) (m/z) 473.3 [M+1]

Workup

  1. washwashed (H2O
  2. dry with materialbrine), dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-59f85d86bc5a48429ff37f08265dec92
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

Loading…