1,1-Dibromoethane → 2-[3-(3-Benzyloxycarbonylamino-propyl)-4-(2-nitro-benzene-sulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester

HRID 1072628Notes

Reaction equation

HRID 1072628 reaction equation
[CH3:1][O:2][C:3](=[O:47])[CH:4]([NH:16][C:17](=[O:46])[CH:18]([NH:33][S:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[N+:43]([O-:45])=[O:44])(=[O:36])=[O:35])[CH2:19][CH2:20][CH2:21][NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[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[CH:49](Br)[CH3:50].C(=O)([O-])[O-].[K+].[K+].OS([O-])(=O)=O.[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:47])[CH:4]([N:16]1[CH2:50][CH2:49][N:33]([S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[N+:43]([O-:45])=[O:44])(=[O:36])=[O:35])[CH:18]([CH2:19][CH2:20][CH2:21][NH:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[C:17]1=[O:46])[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

6

Reactant 4

HCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 516920Potassium bisulfateHCID 208064102-[5-Benzyloxycarbonylamino-2-(2-nitro-benzenesulfonylamino)-pentanoylamino]-3-naphthalen-2-yl-propionic acid methyl ester

Product 1

HCID 208064072-[3-(3-Benzyloxycarbonylamino-propyl)-4-(2-nitro-benzene-sulfonyl)-2-oxo-piperazin-1-yl]-3-naphthalen-2-yl-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 2-[5-benzyloxycarbonylamino-2-(2-nitro-benzenesulfonylamino)-pentanoylamino]-3-naphthalen-2-yl-propionic acid methyl ester, 40, (2.4 g, 3.63 mmol), dibromoethane (3.8 mL, 4.36 mmol), potassium carbonate (5.0 g, 36.3 mmol) in DMF (50 mL) is stirred at 55° C. for 18 hours. The reaction mixture is cooled to room temperature, treated with 1M KHSO4 and the resulting solution is extracted with ethyl acetate. The crude product is purified over silica (sequential elution with EtOAc/hexanes mixtures 1:2,1:1, 100% EtOAc, then EtOAc with 5% MeOH) to afford 2.76 g of the desired product.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionthe resulting solution is extracted with ethyl acetate
  3. customThe crude product is purified over silica (
  4. washsequential elution with EtOAc/hexanes mixtures 1:2,1:1, 100% EtOAc

Sources & evidence

ORD record
ord-27424b7f498c4633930def0990c497da
Source dataset
uspto-grants-2005_06
Patent number
US06911447B2

Reaction notes

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