Cesium carbonate → HCID 69597607, compound

HRID 1796812Notes

Reaction equation

HRID 1796812 reaction equation
[CH2:1]([O:8][C:9](=[O:41])[NH:10][CH:11]([CH3:40])[CH:12]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:28][CH:27]=1)(=[O:25])=[O:24])[C:13]12[O:20][CH2:19][C:16]([CH3:21])([CH2:17][O:18]1)[CH2:15][O:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:49][C:50]([O:52][CH3:53])=[O:51]>CN(C)C=O.C(OCC)(=O)C>[CH3:53][O:52][C:50](=[O:51])[CH2:49][N:22]([S:23]([C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:30][CH:31]=1)(=[O:25])=[O:24])[CH:12]([C:13]12[O:20][CH2:19][C:16]([CH3:21])([CH2:17][O:18]1)[CH2:15][O:14]2)[CH:11]([NH:10][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:41])[CH3:40]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 69597633HCID 69597633, compound

Product 1

HCID 69597607HCID 69597607, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [2-(4-benzyloxy-benzenesulfonylamino)-1-methyl-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid benzyl ester (compound of formula LII, 1.2 g, 2.0 mmol) in 2 ml of dimethylformamide was treated with cesium carbonate (1.12 g, 3.4 mmol) and methyl bromoacetate (0.2 ml, 0.32 g, 2.1 mmol). After stirring for about 2 hours, the mixture was diluted with ethyl acetate, washed 5 times with water, and the organic phase was dried over sodium sulfate, filtered and concentrated, affording 1.3 g of {(4-benzyloxy-benzenesulfonyl)-[2-benzyloxycarbonylamino-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-propyl]-amino}-acetic acid methyl ester (compound of formula LIII) as a colorless syrup.

Workup

  1. washwashed 5 times with water
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d3020dc851184c96af92e53d1a6e082a
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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