Cesium carbonate → HCID 68621706, compound

HRID 2215280Notes

Reaction equation

HRID 2215280 reaction equation
[ClH:1].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:6][C:5]=1[O:15][CH2:16][C@H:17]([OH:33])[CH2:18][NH:19][C:20]([CH3:32])([CH3:31])[CH2:21][CH:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1)#[N:3].C(=O)([O-])[O-].[Cs+].[Cs+].C1OCCOCCOCCOCCOCCOC1.I[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66]>CN(C=O)C>[ClH:1].[CH2:59]([O:13][C:12](=[O:14])[CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]#[N:3])=[C:5]([O:15][CH2:16][C@H:17]([OH:33])[CH2:18][NH:19][C:20]([CH3:31])([CH3:32])[CH2:21][CH:22]2[CH2:23][C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:30]2)[CH:6]=1)[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 123801-IodooctaneHCID 2855718-Crown-6HCID 68607251351490-72-7

Product 1

HCID 68621706HCID 68621706, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of the compound from Example 5 (100 mg, 0.2 mmol) in dry DMF (15 mL) was treated with cesium carbonate (141 mg, 0.4 mmol) and 18-crown-6 (100 mg, 0.41 mmol) followed by 1-iodooctane (144 mg, 0.6 mmol). The resulting mixture was heated at 70° C. under argon for 20 h. The reaction was cooled, concentrated and the residue partitioned between water and ethyl acetate. The organic layer was washed with 10% Na2CO3 (aqueous), brine, dried over MgSO4 and evaporated. Purification by flash chromatography (4% MeOH in CH2Cl2) gave the ester as a yellow oil. The oil in ether was treated with HCl and filtered to give the above titled compound (50 mg, 46%). LC-MS m/e 549.4 [M+H]+.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customthe residue partitioned between water and ethyl acetate
  4. washThe organic layer was washed with 10% Na2CO3 (aqueous), brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customPurification by flash chromatography (4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-81a73694f1fa4757991edb46ab587d38
Source dataset
uspto-grants-2006_09
Patent number
US07109238B2

Reaction notes

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