Tetrahydrofuran → HCID 57642357, compound

HRID 2112494Notes

Reaction equation

HRID 2112494 reaction equation
[Br:1][C:2]1[C:3]([OH:21])=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1.[O:22]1[CH2:26]C[CH2:24][CH2:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>COCCO>[Br:1][C:2]1[C:3]([O:21][CH2:24][CH2:23][O:22][CH3:26])=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 136016305HCID 136016305, compound

Product 1

HCID 57642357HCID 57642357, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent2×

Procedure

To a stirred mixture of 0.300 g (0.00082 mole) 7-bromo-5-(2-chlorophenyl)-1,3-dihydro-8-hydroxy-2H-1,4-benzodiazepin-2-one (Ipp) prepared in Example 28, 60 mL of tetrahydrofuran, 0.070 mL of 2-methoxy ethanol, and 0.2586 g of triphenyl phosphine was added 0.194 mL (0.00099 mole) of diisopropyl azodicarboxylate. The mixture was stirred overnight; then, an additional 0.2586 g of triphenyl phosphine, 0.070 mL of 2-methoxy ethanol and 0.194 mL of diisopropyl azodicarboxylate was added. The mixture stirred for an additional hour and then concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with dichloromethane-methanol (98:2) to yield 0.212 g of 7-bromo-5-(2-chlorophenyl)-1,3-dihydro-8-methoxyethoxy-2H-1,4-benzodiazepin-2-one (Inn). MH+/Z=423.

Workup

  1. stirringThe mixture stirred for an additional hour
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was chromatographed on silica gel eluting with dichloromethane-methanol (98:2)

Sources & evidence

ORD record
ord-505e4e7e576e4317a29f76dcde0ba30c
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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