Hydrochloric Acid → HCID 10506033, compound

HRID 1596366Notes

Reaction equation

HRID 1596366 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH2:19][CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:15]=2[N:14]([CH2:26][C:27]([OH:29])=O)[C:13]1=[O:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH:53]12[CH2:61][CH2:60][CH:57]([CH2:58][CH2:59]1)[CH2:56][NH:55][CH2:54]2.Cl>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH:53]12[CH2:61][CH2:60][CH:57]([CH2:58][CH2:59]1)[CH2:56][N:55]([C:27]([CH2:26][N:14]1[C:15]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:16]=3[C:17]([CH2:19][CH3:20])=[N:18][CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[C:13]1=[O:30])=[O:29])[CH2:54]2

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 92403-Azabicyclo[3.2.2]nonaneHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11795781HCID 11795781, compound

Product 1

HCID 10506033HCID 10506033, compoundYield 79.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3RS)-3-benzyloxycarbonylamino-5-ethyl-2,3-dihydro-1-carboxymethyl-9-methyl-1H-1,4-benzodiazepin-2-one (1.22 g), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (642 mg), 1-hydroxybenzotriazole (453 mg), 3-azabicyclo[3.2.2]nonane (419 mg) and triethylamine (1.55 ml) in N,N-dimethylformamide (30 ml) was stirred at room temperature overnight. Ethyl acetate and 0.1N aqueous hydrochloric acid were added to the reaction mixture, which was stirred for several minutes. The separated organic layer was washed with 1N aqueous hydrochloric acid, water twice, a saturated aqueous solution of sodium bicarbonate and brine, successively, and then dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was triturated in diisopropyl ether and collected by filtration to afford (3RS)-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-3-benzyloxycarbonylamino-2,3-dihydro-5-ethyl-9-methyl-1H-1,4-benzodiazepin-2-one (1.23 g, 79.9%) as a crystalline powder.

Workup

  1. stirringwas stirred for several minutes
  2. washThe separated organic layer was washed with 1N aqueous hydrochloric acid, water twice
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and brine, successively, and then dried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was triturated in diisopropyl ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e60fd90bd700472ba3daa788cd7ada89
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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