HCID 58633500, compound → HCID 58633548, compound

HRID 1825323Notes

Reaction equation

HRID 1825323 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:17][C:18]([C:20]1([CH2:25][C@@H:26]([CH2:30][CH2:31][CH3:32])[C:27]([OH:29])=[O:28])[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19])[CH2:11][C:12]([O:14]CC)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[Na+].CO>[CH2:1]([O:8][CH2:9][C@@H:10]([NH:17][C:18]([C:20]1([CH2:25][C@@H:26]([CH2:30][CH2:31][CH3:32])[C:27]([OH:29])=[O:28])[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19])[CH2:11][C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 58633500HCID 58633500, compound

Product 1

HCID 58633548HCID 58633548, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of the ethyl ester from example 17 (70 mg, 0.16 mmol) in sodium hydroxide solution (1 ml, 1N) and methanol (5 ml) was stirred at room temperature for 18 hours. The reaction was concentrated under reduced pressure to remove the methanol, and the residue was partitioned between ethyl acetate (10 ml) and hydrochloric acid (2N, 10 ml). The phases were separated, the aqueous layer extracted with ethyl acetate (4×10 ml), the combined organic solutions washed with brine (10 ml), dried (MgSO4) and evaporated under reduced pressure to afford the title compound, 50 mg; 1H NMR (CDCl3, 400 MHz) δ: 0.92 (t, 3H), 1.23–2.39 (m, 15H), 2.74 (d, 2H), 3.60 (m, 2H), 4.52 (m, 3H), 6.66 (d, 1H), 7.35 (m, 5H); HRMS: m/z (ES+) 420.2374 [MH+]; C23H33NO6 calculated 420.2381.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customto remove the methanol
  3. customthe residue was partitioned between ethyl acetate (10 ml) and hydrochloric acid (2N, 10 ml)
  4. customThe phases were separated
  5. extractionthe aqueous layer extracted with ethyl acetate (4×10 ml)
  6. washthe combined organic solutions washed with brine (10 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9d61ff3d4e4749e3a381c2f0598cc873
Source dataset
uspto-grants-2006_05
Patent number
US07045653B2

Reaction notes

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