Chloromethyl Methyl Ether → HCID 67227538, compound

HRID 1848848Notes

Reaction equation

HRID 1848848 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH2:10][C:9]=2[CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:25]([O:34][C:35]4[CH:40]=[CH:39][CH:38]=[C:37]([OH:41])[C:36]=4[CH3:42])[CH:24]=3)[CH2:19][CH2:18]2)=[CH:4][CH:3]=1.Cl[CH2:44][O:45][CH3:46].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][C:12]([CH3:14])([CH3:15])[CH2:11][CH2:10][C:9]=2[CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:25]([O:34][C:35]4[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH2:44][O:45][CH3:46])[C:36]=4[CH3:42])[CH:24]=3)[CH2:19][CH2:18]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 10796Cesium carbonateHCID 67228558HCID 67228558, compound

Product 1

HCID 67227538HCID 67227538, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of EXAMPLE 158B (0.6 g), chloro(methoxy)methane (0.18 g) and cesium carbonate (0.9 g) was suspended in N,N-dimethylformamide (15 mL). After it stirred at room temperature for 30 minutes, the crude product was purified by preparative HPLC using a 250×50 mm C18 column and eluting with 20-100% CH3CN vs. 0.1% trifluoroacetic acid in water.

Workup

  1. customthe crude product was purified by preparative HPLC
  2. washeluting with 20-100% CH3CN vs

Sources & evidence

ORD record
ord-1362640d6187497eb1f87357efb07939
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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