Water → HCID 57847193, compound

HRID 735769Notes

Reaction equation

HRID 735769 reaction equation
[C:1]1([C@H:7]2[C@H:16]3[CH2:17][CH2:18][N:19]([C:20]([C@H:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]4[NH:28][C:29]([C:31]4[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=4[C:33]([OH:35])=O)=[O:30])=[O:21])[C@H:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.CCOC(OC(OCC)=O)=O.O>CN(C=O)C>[C:1]1([C@H:7]2[C@H:16]3[CH2:17][CH2:18][N:19]([C:20]([C@H:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]4[N:28]4[C:33](=[O:35])[C:32]5[C:31](=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:29]4=[O:30])=[O:21])[C@H:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 57846916HCID 57846916, compound

Product 1

HCID 57847193HCID 57847193, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound (70 mg, 0.13 mmol) of Example 123 and triethylamine (20.9 μl, 0.15 mmol) in DMF (5 ml) was added DEPC (24.5 μl, 0.15 mmol) under ice-cooling, and the mixture was stirred at room temperature for 4 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate, the extract was washed with saturated brine and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (3:1-1:1, v/v) to give the title compound (54 mg, 71%) as a white solid.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated under reduced pressure
  6. washeluted with hexane-ethyl acetate (3:1-1:1

Sources & evidence

ORD record
ord-64492ceebacd4c2bafe6668cdf5ec67b
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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