(3RS)-3-amino-1-ethoxycarbonylmethyl-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one → 5-(2-Fluorophenyl)-2,5-dihydro-3-((((1-methylethyl) amino)carbonyl)amino)-2-oxo-1H-1,4-benzodiazepine-1-acetic acid ethyl ester

HRID 620598Notes

Reaction equation

HRID 620598 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[N:4]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:3]1=[O:26]>O1CCCC1>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][N:4]1[C:5]2[CH:19]=[CH:18][CH:17]=[CH:16][C:6]=2[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[N:8]=[C:2]([NH:1][C:3]([NH:4][CH:5]([CH3:19])[CH3:6])=[O:26])[C:3]1=[O:26])[CH3:25]

Participants

3

Reactant 1

HCID 10066773(3RS)-3-amino-1-ethoxycarbonylmethyl-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Product 1

HCID 541261305-(2-Fluorophenyl)-2,5-dihydro-3-((((1-methylethyl) amino)carbonyl)amino)-2-oxo-1H-1,4-benzodiazepine-1-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Equimolar amounts of 3(R,S)-amino-1,3-dihydro-1-ethoxycarbonylmethyl-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one and isoproplylisocyanate were mixed in 8 ml of dry tetrahydrofuran at room temperature. The reaction mixture was allowed to stand for 8 hours and was then filtered. The collected solids were washed with tetrahydrofuran and dried in vacuo over P2O5 to give the analytical product: m.p. 155°-157° C.

Workup

  1. filtrationwas then filtered
  2. washThe collected solids were washed with tetrahydrofuran
  3. dry with materialdried in vacuo over P2O5
  4. customto give the analytical product

Sources & evidence

ORD record
ord-cde87df2688143729befaef06043eadd
Source dataset
uspto-grants-1989_04
Patent number
US04820834

Reaction notes

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