Hydrochloric Acid → HCID 10071233, compound

HRID 1110201Notes

Reaction equation

HRID 1110201 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([O:7]CC1C=CC=CC=1)=[O:6].C(N(CC)CC)C.[CH3:25][N:26]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[C:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:29][C@@H:28]([NH:43][C:44](OC2C=CC([N+]([O-])=O)=CC=2)=[O:45])[C:27]1=[O:56].Cl>CN(C=O)C.C(O)C.[Pd].O>[CH3:25][N:26]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[C:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:29][C@@H:28]([NH:43][C:44]([NH:1][C:2]2[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=2)[C:5]([OH:7])=[O:6])=[O:45])[C:27]1=[O:56]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 9980117HCID 9980117, compoundHCID 15428374Benzyl 3-aminobenzoate

Product 1

HCID 10071233HCID 10071233, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To benzyl m-aminobenzoate (0.25 g, 1.10 mmole) in DMF (17 ml) was added triethylamine (0.23 ml) followed by a solution of (R)-1,3-dihydro-1-methyl-3-(p-nitrophenyloxycarbonyl)amino-5-phenyl-2H-1,4-benzodiazepin-2-one (0.469 g, 1.09 mmole) in DMF (23 ml) containing triethylamine (0.23 ml). The mixture was stirred at room temperature for one hour, then treated with water, made acidic with 1N HCl, and extracted with ethyl acetate. The ethyl acetate layers were combined, washed with aqueous sodium bicarbonate, dried over sodium sulfate, filtered, and evaporated to dryness in vacuo. The residue was chromatographed on silica gel eluted with 500 ml each of 5%, 6%, 7%, 9%, 10%, and 12% ether in CH2Cl2. The product fractions were combined and evaporated to dryness in vacuo. A portion of the residue (81.2 mg, 0.086 mmole) was dissolved in ethanol (70 ml) and hydrogenated over palladium/charcoal (20 mg) at 50 psi of H2. The mixture wag filtered and evaporated to dryness in vacuo to provide the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with aqueous sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. customThe residue was chromatographed on silica gel
  7. washeluted with 500 ml each of 5%, 6%, 7%, 9%, 10%, and 12% ether in CH2Cl2
  8. customevaporated to dryness in vacuo
  9. filtrationThe mixture wag filtered
  10. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-173643a16ff748cbae8deadc9aab1672
Source dataset
uspto-grants-1994_06
Patent number
US05324726

Reaction notes

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