HCID 178474737, compound → HCID 178474736, compound

HRID 1613498Notes

Reaction equation

HRID 1613498 reaction equation
C([O:5][C:6](=[O:34])[CH:7]([CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:33])[CH3:32])[CH2:8][C:9]1([C:14](=[O:25])[NH:15][C@H:16]2[CH2:21][CH2:20][C@@H:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C>FC(F)(F)C(O)=O>[C:31]([NH:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:7]([CH2:8][C:9]1([C:14](=[O:25])[NH:15][C@H:16]2[CH2:21][CH2:20][C@@H:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]2)[CH2:10][CH2:11][CH2:12][CH2:13]1)[C:6]([OH:34])=[O:5])(=[O:33])[CH3:32]

Participants

3

Reactant 1

HCID 178474737HCID 178474737, compound

Product 1

HCID 178474736HCID 178474736, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(4-Acetamidobutyl)-3-{1-[(cis-4-carboxy-cyclohexyl)carbamoyl]cyclopentyl}propanoic acid t-butyl ester (270 mg, 0.58 mmole) was dissolved in trifluoroacetic acid (4 ml) at 0° C. After 20 hours the solvent was evaporated and the resulting oil azeotroped with dichloromethane (3×20 ml). The oil was taken up in ethyl acetate (20 ml) and washed with water (7×20 ml) until the washings were neutral. The organic layer was separated, dried over magnesium sulphate, and evaporated. The residue was dissolved in saturated sodium carbonate solution (20 ml) washed with ethyl acetate (2×20 ml), acidified with 2N hydrochloric acid and then extracted with ethyl acetate (3×20 ml). The organic layer was separated, dried over magnesium sulphate and evaporated. The residue was azeotroped with tetrahydrofuran to give the title product as a colourless foam (110 mg, 45%). Found: C,62.58; H,8.71; N,5.27. C22H36N2O5.C4H8O requires C,62.88; H,8.93; N,5.64%.

Workup

  1. customAfter 20 hours the solvent was evaporated
  2. customthe resulting oil azeotroped with dichloromethane (3×20 ml)
  3. washwashed with water (7×20 ml) until the washings
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. dissolutionThe residue was dissolved in saturated sodium carbonate solution (20 ml)
  8. washwashed with ethyl acetate (2×20 ml)
  9. extractionextracted with ethyl acetate (3×20 ml)
  10. customThe organic layer was separated
  11. dry with materialdried over magnesium sulphate
  12. customevaporated
  13. customThe residue was azeotroped with tetrahydrofuran

Sources & evidence

ORD record
ord-2bb0f969c24a4f03ab5133d69ffeb4de
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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