1,2-Dichloroethane → HCID 69540415, compound

HRID 1700110Notes

Reaction equation

HRID 1700110 reaction equation
Cl.[O:2]=[C:3]1[C@@H:9]([NH2:10])[CH2:8][C:7](=[O:11])[C:6]2[CH:12]=[CH:13][CH:14]=[CH:15][C:5]=2[N:4]1[CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].[CH3:27][C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([CH3:38])[C:36]=1[OH:37])[C:31](O)=[O:32].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl.CCOC(C)=O>[O:2]=[C:3]1[C@@H:9]([NH:10][C:31](=[O:32])[C:30]2[CH:34]=[C:35]([CH3:38])[C:36]([OH:37])=[C:28]([CH3:27])[CH:29]=2)[CH2:8][C:7](=[O:11])[C:6]2[CH:12]=[CH:13][CH:14]=[CH:15][C:5]=2[N:4]1[CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18]

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 1383874-Hydroxy-3,5-dimethylbenzoic acidHCID 22948699HCID 22948699, compound

Product 1

HCID 69540415HCID 69540415, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 13a and 3,5-dimethyl-4-hydroxybenzoic acid (307 mg, 1.85 mmol) in 5 ml each of DMF and CH2Cl2 was added HOBT (250 mg, 1.85 mmol), EDC (421 mg, 2.2 mmol), and triethylamine (0.64 ml, 4.56 mmol). The reaction was stirred at room temp. for 18 hrs. then diluted with EtOAc (150 ml) and washed with 10% NaHSO4, sat. NaHCO3 and sat. NaCl. The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated in vacuo to afford a gum that was purified by flash chromatography eluting with CH2Cl2/EtOAc (7/3) to afford 545 mg (62%) of the title compound.

Workup

  1. washwashed with 10% NaHSO4, sat. NaHCO3 and sat. NaCl
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto afford a gum that
  6. customwas purified by flash chromatography
  7. washeluting with CH2Cl2/EtOAc (7/3)

Sources & evidence

ORD record
ord-32c88bc2bd494a339a09138c8deda2b2
Source dataset
uspto-grants-2002_02
Patent number
US06350741B1

Reaction notes

Loading…