Potassium Carbonate → HCID 88605383, compound

HRID 2107846Notes

Reaction equation

HRID 2107846 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:26]/[O:27][C:28]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)/[C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([OH:23])=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C1OCCOCCOCCOCCOCCOC1.C([O-])([O-])=O.[K+].[K+].[C:71](=[O:83])([O:79][CH:80](I)[CH3:81])[O:72][CH:73]1[CH2:78][CH2:77][CH2:76][CH2:75][CH2:74]1>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:26]/[O:27][C:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)/[C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([O:23][CH:80]([O:79][C:71]([O:72][CH:73]4[CH2:78][CH2:77][CH2:76][CH2:75][CH2:74]4)=[O:83])[CH3:81])=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 111092781-Iodoethyl cyclohexyl carbonateHCID 88600620HCID 88600620, compound

Product 1

HCID 88605383HCID 88605383, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the product of Procedure 7 (35 g, 53.7 mmol) 18-crown-6 (4.0 g, 15 mmol) and well ground K2CO3 (9.45 g, 6.84 mmol) in dry DMF (330 ml) was added dropwise the cyclohexyl 1-iodoethyl carbonate (41 g, 138 mmol) at 0° C. under argon and the mixture was stirred for 1 hr. at 2°-4° C. The mixture was diluted with ethyl acetate (1.5 L) and washed well with water. The organic layer was separated, dried and evaporated under reduced pressure. The residue was chromatographed on a column of silica gel (400 g) and the column was eluted with n-hexane-dichloromethane (2:1 to 0:1). The fractions containing the desired product were combined and evaporated under reduced pressure to afford 27.3 g (62%) of the product as an amorphous powder.

Workup

  1. customat 2°-4° C
  2. washwashed well with water
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed on a column of silica gel (400 g)
  7. washthe column was eluted with n-hexane-dichloromethane (2:1 to 0:1)
  8. additionThe fractions containing the desired product
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-967ea5ab85ac4a8ba5ff25920507e3e4
Source dataset
uspto-grants-1990_06
Patent number
US04935508

Reaction notes

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