Acetic Acid → HCID 69212176, compound

HRID 1392157Notes

Reaction equation

HRID 1392157 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C@@:7]23[CH2:14][C@@H:13]([OH:15])[CH2:12][N:11]2[C:10](=[O:16])[N:9]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=2)[C:8]3=[O:25])=[CH:4][CH:3]=1.[CH3:28][CH2:29][O:30]C(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@:7]23[CH2:14][C@H:13]([O:15][C:29](=[O:30])[CH3:28])[CH2:12][N:11]2[C:10](=[O:16])[N:9]([C:17]2[CH:18]=[C:19]([Cl:24])[CH:20]=[C:21]([Cl:23])[CH:22]=2)[C:8]3=[O:25])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 59124109HCID 59124109, compound

Product 1

HCID 69212176HCID 69212176, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5S,7R)-5-(4-bromobenzyl)-3-(3,5-dichlorophenyl)-7-hydroxy-1,3-diazabicyclo[3.3.0]octane-2,4-dione (0.21 g) in THF (5 mL) was added DEAD (0.09 mL), triphenylphosphine (0.15 g), and acetic acid (0.035 mL). After stirring overnight at room temperature, the mixture was concentrated. Purification by chromatography (Silica gel: 25% EtOAc/hexane, Chromatotron) afforded the titled compound (0.151 g). MS (m/z) 511 (MH+), mp 149.8° C.

Workup

  1. concentrationthe mixture was concentrated
  2. customPurification by chromatography (Silica gel: 25% EtOAc/hexane, Chromatotron)

Sources & evidence

ORD record
ord-7198bd381a3e430281a76fc7cb80cca1
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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