HCID 178457031, compound → HCID 178457030, compound

HRID 1655603Notes

Reaction equation

HRID 1655603 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[N:14]=[C:13]([N:15]([CH2:34][CH2:35][CH3:36])[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]4[NH:33][N:32]=[N:31][N:30]=4)=[CH:19][CH:18]=3)[C:12]([C:37]([O:39]CC3C=CC=CC=3)=[O:38])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[OH-].[Na+]>[CH2:7]([O:8][C:9]1[N:14]=[C:13]([N:15]([CH2:34][CH2:35][CH3:36])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[NH:33][N:32]=[N:31][N:30]=3)=[CH:19][CH:18]=2)[C:12]([C:37]([OH:39])=[O:38])=[CH:11][CH:10]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 178457031HCID 178457031, compound

Product 1

HCID 178457030HCID 178457030, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

The resultant more polar methyl ester from Example 217A (10.4 mg, 19.5 μmol) was dissolved in 0.1 mL of methanol and 0.09 mL 1.0M aqueous sodium hydroxide. The solution was heated (in a sealed vial) at 80° C. for 28 hours, then cooled and concentrated to an aqueous residue by means of a stream of nitrogen. The residue was partitioned between 5 mL of methylene chloride and 2 mL 1.0M aqueous sodium hydrogen sulfate, then the aqueous phase was extracted with 2×2 mL methylene chloride. The combined organic phases were washed with 2 mL brine, dried through a plug of sodium sulfate, and evaporated under high vacuum to provide a colorless glass. Purification by preparative TLC (1% HOAc in 1:1 CH2Cl2 -EtOAc) produced 9.0 mg (17.3 μmol, 89%) of the title compound as a colorless glass. m.p. 68°-82° C. 1H NMR (CDCl3, 300 MHz) d 0.88 (t, J=7.5 Hz, 3H), 1.37-1.52 (br m, 2H), 3.21-3.31 (br m, 2H), 4.12 (s, 2H), 5.49 (s, 2H), 6.65 (d, J=7.5 Hz, 2H), 6.77 (d, J=9 Hz, 1H), 6.86 (d, J= 7.5 Hz, 2H), 7.20-7.55 (m, 10H), 7.84 (dd, J=1.5, 7 Hz, 1H), 8.25 (d, J=7.5 Hz, 1H). MS (DCl/NH3) m/e 521 (M+H)+.

Workup

  1. temperaturecooled
  2. concentrationconcentrated to an aqueous residue by means of a stream of nitrogen
  3. customThe residue was partitioned between 5 mL of methylene chloride and 2 mL 1.0M aqueous sodium hydrogen sulfate
  4. extractionthe aqueous phase was extracted with 2×2 mL methylene chloride
  5. washThe combined organic phases were washed with 2 mL brine
  6. dry with materialdried through a plug of sodium sulfate
  7. customevaporated under high vacuum
  8. customto provide a colorless glass
  9. customPurification by preparative TLC (1% HOAc in 1:1 CH2Cl2 -EtOAc)

Sources & evidence

ORD record
ord-3d9800be68c84e84bfaf79951d5dae3b
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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