1,2-Dibromoethane → (S,S)-2-[3-Allyl-4-(2-nitro-benzenesulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester

HRID 720161Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([NH:16][C:17](=[O:35])[C@@H:18]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N+:32]([O-:34])=[O:33])(=[O:25])=[O:24])[CH2:19][CH:20]=[CH2:21])[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.Br[CH2:38][CH2:39]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([N:16]1[CH2:39][CH2:38][N:22]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N+:32]([O-:34])=[O:33])(=[O:25])=[O:24])[C@@H:18]([CH2:19][CH:20]=[CH2:21])[C:17]1=[O:35])[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of (S,S)-3-naphthalen-2-yl-2-[2-(2-nitro-benzenesulfonylamino)-pent-4-enoylamino]-propionic acid methyl ester, 3, (3.6 g, 7.0 mmol) and 1,2-dibromoethane (13.2 g, 70.0 mmol) in DMF (40 mL) is added potassium carbonate (9.6 g, 70.0 mmol). The reaction suspension was stirred at 65° C. for 12 h, quenched with 10% aqueous HCl and extracted with EtOAc. The extract is dried over Na2SO4, concentrated and the residue purified over silica gel (hexanes/EtOAc,1:2) to afford 3.7 g (97% yield) of the desired product.

Workup

customquenched with 10% aqueous HCl
extractionextracted with EtOAc
dry with materialThe extract is dried over Na2SO4
concentrationconcentrated
customthe residue purified over silica gel (hexanes/EtOAc,1:2)

Sources & evidence

ORD record: ord-87185421daa0488cbd038d584eccc41a
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132539B2

Reaction notes

Loading…