Hydrochloric Acid → (3RS)-Amino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one

HRID 2339Notes

Reaction equation

HRID 2339 reaction equation
C(OC([NH:6][CH:7]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:11]2[CH:20]=[CH:21][CH:22]=[CH:23][C:10]=2[N:9]([CH2:24][C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])=[O:26])[C:8]1=[O:31])=O)C.Cl>C(Cl)Cl>[NH2:6][CH:7]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:11]2[CH:20]=[CH:21][CH:22]=[CH:23][C:10]=2[N:9]([CH2:24][C:25]([C:27]([CH3:29])([CH3:28])[CH3:30])=[O:26])[C:8]1=[O:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10740914(3RS)-Ethyloxycarbonylamino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one

Product 1

HCID 10498048(3RS)-Amino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-oneYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3RS)-ethoxycarbonylamino-1-(tert-butylcarbonylmethyl)-2,3-dihydro-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one (10.0 g, 23.7 mmol) in DCM (40 ml) was added to the above solution below 25° C. and the mixture was stirred for 50 h. The mixture was then poured into 3M HCl (80 ml) below 25° C. and the aqueous portion was washed with DCM (10 ml×2). The combined organic portions were extracted with 3M HCl (20 ml). DCM (50 ml) was added to the combined aqueous portions and the mixture was basified to pH 10 with 25% NaOH below 5° C. The organic portion was washed with brine (50 ml) and evaporated. CH3CN (50 ml) was added and the mixture was filtered to remove the small amount of insoluble material. The filtrate was evaporated to give the rifle compound as a brown foam (7.75 g, 93%), which was not purified further.

Workup

  1. washthe aqueous portion was washed with DCM (10 ml×2)
  2. extractionThe combined organic portions were extracted with 3M HCl (20 ml)
  3. additionDCM (50 ml) was added to the combined aqueous portions
  4. customwas basified to pH 10 with 25% NaOH below 5° C
  5. washThe organic portion was washed with brine (50 ml)
  6. customevaporated
  7. additionCH3CN (50 ml) was added
  8. filtrationthe mixture was filtered
  9. customto remove the small amount of insoluble material
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-ddb2942de49c4b9a90cdb5a3cda50c77
Source dataset
uspto-grants-1998_03
Patent number
US05728829

Reaction notes

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