Sodium Carbonate → HCID 15017687, compound

HRID 2352090Notes

Reaction equation

HRID 2352090 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:30]/[O:31][C:32](=[O:34])[CH3:33])/[C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:25]([OH:27])=[O:26])=[C:15](/[CH:18]=[CH:19]\[CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C([O-])([O-])=O.[Na+].[Na+].[C:41]([O:44][CH:45](Br)[CH3:46])(=[O:43])[CH3:42]>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:30]/[O:31][C:32](=[O:34])[CH3:33])/[C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:25]([O:27][CH:45]([O:44][C:41](=[O:43])[CH3:42])[CH3:46])=[O:26])=[C:15](/[CH:18]=[CH:19]\[CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 111375051-Bromoethyl acetate2×HCID 15017684HCID 15017684, compound

Product 1

HCID 15017687HCID 15017687, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of the product of Example 68 (248 mg, 0.49 mmol) in 25 ml of dry DMF was added Na2CO3 (51 mg, 0.49 mmol) and 1-acetoxyethyl bromide (82 mg, 0.49 mmol) at -10° C. The mixture was stirred at 5° C. for 30 min and 82 mg (0.49 mmol) of 1-acetoxyethyl bromide was added to the suspension. After being stirred for 30 min more, the reaction mixture was diluted with AcOEt (50 ml), washed with water (30 ml×3) and brine, dried over MgSO4 and evaporated under diminished pressure. The crude product was purified by silica gel chromatography eluted with 3% MeOH in chloroform. Removal of the solvent from appropriate eluant followed by freeze-drying gave 157 mg (54%) of the title compound, mp 125° C. (dec). IR νmax (KBr) cm-1 3430, 3290, 1770, 1680. UV λmax (pH 7 phosphate buffer) nm (ε) 228 (21900), 287 (12700). 1H NMR (DMSO-d6) δ 1.51 (3H, d, J=6 Hz, 4-COOCHCH3), 2.02 (3H, s, AcO), 2.06 (3H, s, AcO), 2.22 (3H, s, AcO), 3.47 (2H, br.s, 2-H), 4.46 (1H, q, J=6 Hz, 4-COOCHCH3), 4.55 (2H, ABq, CH2OAc), 5.12 (1H, d, J=5 Hz, 6-H), 5.70 (1H, m, 3-CH=CH), 5.95 (1H, dd, J=5 & 7 Hz, 7-H), 6.25 (1H, d, J=12 Hz, 3-CH=CH), 6.92 (1H, s, thiazole).

Workup

  1. stirringAfter being stirred for 30 min more
  2. washwashed with water (30 ml×3) and brine
  3. dry with materialdried over MgSO4
  4. customevaporated under diminished pressure
  5. customThe crude product was purified by silica gel chromatography
  6. washeluted with 3% MeOH in chloroform
  7. customRemoval of the solvent from appropriate eluant
  8. customby freeze-drying

Sources & evidence

ORD record
ord-d247ffbee56c48b4b878cf5dc072e3f0
Source dataset
uspto-grants-1989_10
Patent number
US04874856

Reaction notes

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