3-Amino-3-Oxopropanoic Acid → (5S,7S)-5-(4-Cyanobenzyl)-3-(3,5-dichlorophenyl)-7-[(2-carbamoylacetyl)amino]-1,3-diazabicyclo[3.3.0]octane-2,4-dione

HRID 2223332Notes

Reaction equation

HRID 2223332 reaction equation
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][C@@:8]23[CH2:15][C@H:14]([NH2:16])[CH2:13][N:12]2[C:11](=[O:17])[N:10]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[C:9]3=[O:26])=[CH:5][CH:4]=1)#[N:2].[C:29](O)(=[O:34])[CH2:30][C:31]([NH2:33])=[O:32].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1.C(Cl)CCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C@@:8]23[CH2:15][C@H:14]([NH:16][C:29](=[O:34])[CH2:30][C:31](=[O:32])[NH2:33])[CH2:13][N:12]2[C:11](=[O:17])[N:10]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=2)[C:9]3=[O:26])=[CH:27][CH:28]=1)#[N:2]

Participants

7

Reactant 4

HCID 753673-Amino-3-Oxopropanoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11281440(5S,7S)-5-(4-cyanobenzyl)-3-(3,5-dichlorophenyl)-7-amino-1,3-diazabicyclo[3.3.0]octane-2,4-dione

Product 1

HCID 11454827(5S,7S)-5-(4-Cyanobenzyl)-3-(3,5-dichlorophenyl)-7-[(2-carbamoylacetyl)amino]-1,3-diazabicyclo[3.3.0]octane-2,4-dioneYield 88%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (5S,7S)-5-(4-cyanobenzyl)-3-(3,5-dichlorophenyl)-7-amino-1,3-diazabicyclo[3.3.0]octane-2,4-dione (200 mg), malonamic acid (59.5 mg), EDC (112 mg), HOBT (97.5 mg) and DIEA (168 μL) in THF (5 mL) was stirred overnight at room temperature. The reaction mixture was evaporated. The residue was dissolved in EtOAc and the resulting solution was washed with water, saturated aqueous NaHCO3 solution, brine, dried (Na2SO4) and concentrated to give 212 mg of the titled compound. MS (m/z) 500 (MH+).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe resulting solution was washed with water, saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0366f08fe5ef41eb97ad6555de644daf
Source dataset
uspto-grants-2008_05
Patent number
US07375128B2

Reaction notes

Loading…