1,2-Dichloroethane → HCID 68638762, compound

HRID 1253876Notes

Reaction equation

HRID 1253876 reaction equation
FC(F)(F)C([O-])=O.[CH2:8]([O:15][C:16]([N:18]([CH2:23][C:24]1[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:25]=1[NH3+:32])[CH2:19][C:20](O)=[O:21])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[F:30][C:28]1[C:27]([F:31])=[CH:26][C:25]2[NH:32][C:20](=[O:21])[CH2:19][N:18]([C:16]([O:15][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:17])[CH2:23][C:24]=2[CH:29]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68628325HCID 68628325, compound

Product 1

HCID 68638762HCID 68638762, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(benzyloxycarbonyl-carboxymethyl-amino)-methyl]-4,5-difluoro-phenyl-ammonium trifluoroacetate (4.75 g, 10.25 mmol) in DCM (40 mL) was added EDC (2.55 g, 13.32 mmol) and HOBT (1.7.9 g, 13.32 mmol) at 0° C. The resulting solution was stirred for 5 min and DIPEA (5.35 mL, 30.75 mmol) was added to it. The reaction mixture was stirred overnight at r.t. under argon. After completion of the reaction as confirmed by TLC, water (60 mL) was added to the reaction mixture and crude compound was extracted with DCM (3×50 mL). The combined organic layers were dried over Na2SO4 and the solvents were removed in vacuo to afford the crude compound which was purified by column chromatography (silica gel: 2:8 EtOAc:Pet. ether) to afford pure benzyl 7,8-difluoro-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate (2.04 g, 60%) as thick gel.

Workup

  1. stirringThe reaction mixture was stirred overnight at r.t. under argon
  2. customAfter completion of the reaction
  3. additionwas added to the reaction mixture and crude compound
  4. extractionwas extracted with DCM (3×50 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customthe solvents were removed in vacuo
  7. customto afford the crude compound which
  8. customwas purified by column chromatography (silica gel: 2:8 EtOAc:Pet. ether)

Sources & evidence

ORD record
ord-897e993943c042749e95480c9c9c7c73
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

Loading…