Succinamic acid → (5S,7S)-5-(4-Cyanobenzyl)-3-(3,5-dichlorophenyl)-7-[(3-carbamoylpropionyl)amino]-1,3-diazabicyclo[3.3.0]octane-2,4-dione

HRID 2223331Notes

Reaction equation

HRID 2223331 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:35])[CH2:30][CH2:31][C:32]([NH2:34])=[O:33].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:35])[CH2:30][CH2:31][C:32](=[O:33])[NH2:34])[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 12522Succinamic 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 10239341(5S,7S)-5-(4-Cyanobenzyl)-3-(3,5-dichlorophenyl)-7-[(3-carbamoylpropionyl)amino]-1,3-diazabicyclo[3.3.0]octane-2,4-dioneYield 70.3%

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 (82.7 mg), succinamic acid (45.86 mg), EDC (93.12 mg), HOBT (61.24 mg) and DIEA (104.79 μL) in THF (5 mL) was stirred overnight at room temperature. The reaction mixture was concentrated and purified by high performance liquid chromatography (HPLC) (Beckman 5μ C18 column; eluted with a gradient of H2O/MeCN (10-100%)/0.1% TFA) to give 72 mg of the titled compound. MS (m/z) 536 (MNa+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by high performance liquid chromatography (HPLC) (Beckman 5μ C18 column
  3. washeluted with a gradient of H2O/MeCN (10-100%)/0.1% TFA)

Sources & evidence

ORD record
ord-dbd7c1e47bb64ee990132b77bc035511
Source dataset
uspto-grants-2008_05
Patent number
US07375128B2

Reaction notes

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