1,2-Dichloroethane → HCID 54232406, compound

HRID 1274985Notes

Reaction equation

HRID 1274985 reaction equation
C(Cl)CCl.[C:5]([C:8]1[CH:9]=[CH:10][C:11]2[NH:17][CH:16]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:15](=[O:23])[N:14](C)[CH2:13][C:12]=2[CH:25]=1)([OH:7])=O.C1[CH:27]=[CH:28][C:29]2N(O)[N:33]=[N:32][C:30]=2[CH:31]=1.O.CC[N:39](C(C)C)[CH:40]([CH3:42])C.C[N:47](C=O)C>>[CH3:31][C:30]1[N:32]=[N:33][C:27]([NH:39][CH2:40][CH2:42][NH:47][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[NH:17][CH:16]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:15](=[O:23])[N:14]=[CH:13][C:12]=3[CH:25]=2)=[O:7])=[CH:28][CH:29]=1

Participants

7

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 23505570Methyl 7-carboxy-2,3,4,5-tetrahydro-4-methyl-3-oxo-1h-1,4-benzodiazepine-2-acetate

Product 1

HCID 54232406HCID 54232406, compoundYield 63%

Procedure

EDC (759 mg, 3.96 mmol) was added to a solution of the compound of Preparation BB(b) (3.6 mmol), methyl (±)-7-carboxy-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetate (1.05 g, 3.6 mmol), HOBT.H2O (535 mg, 3.96 mmol), and DIEA (2.07 mL, 11.88 mmol) ion anhydrous DMF at RT. After 20 h, the reaction was concentrated, and the residue was dissolved in CH2Cl2 and chromatographed (silica gel, step gradient 0-10%, CH3OH/CH2Cl2) to give the title compound as a pale yellow solid (960 mg, 63%): MS(ES) m/e 427 [M+H]+.

Workup

  1. customat RT
  2. concentrationthe reaction was concentrated
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. customchromatographed (silica gel, step gradient 0-10%, CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-5f07beb4ba5f403682699c36f81e6fb2
Source dataset
uspto-grants-2000_12
Patent number
US06159964

Reaction notes

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