HCID 178450994, compound → HCID 178510974, compound

HRID 1613497Notes

Reaction equation

HRID 1613497 reaction equation
C([O:5][C:6](=[O:31])[CH:7]([CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])[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>[NH2:30][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:31])=[O:5]

Participants

3

Reactant 1

HCID 178450994HCID 178450994, compound

Product 1

HCID 178510974HCID 178510974, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(4-Aminobutyl)-3-{1-[(cis-4-carboxy-cyclohexyl)carbamoyl]cyclopentyl}propanoic acid t-butyl ester (1.0 g, 2.28 mmole) was dissolved in trifluoroacetic acid (8 ml) at 0° C. After 3 days at this temperature the solvent was evaporated and the residue azeotroped with dichloromethane (3×50 ml). The resulting brown oil was purified by passage through ion exchange resin (Bio-Rad AG 50W-X8, 30 ml) eluting with pyridine and water (3:100 by volume), and the appropriate fractions evaporated to give the title product as a colourless foam (700 mg, 80%). Found: C,61.97; H,9.08; N,7.69. C20H34N2O5, 0.1 C5H5N, 0.3 H2O requires C,62.21; H,8.94; N,7.43%.

Workup

  1. customAfter 3 days at this temperature the solvent was evaporated
  2. customthe residue azeotroped with dichloromethane (3×50 ml)
  3. customThe resulting brown oil was purified by passage through ion exchange resin (Bio-Rad AG 50W-X8, 30 ml)
  4. washeluting with pyridine and water (3:100 by volume)
  5. customthe appropriate fractions evaporated

Sources & evidence

ORD record
ord-22c67fddfa31490abdf5e37208350a9d
Source dataset
uspto-grants-1993_03
Patent number
US05192800

Reaction notes

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