Triethylamine → HCID 178450995, compound

HRID 1086727Notes

Reaction equation

HRID 1086727 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH:7]([CH2:17][CH2:18][CH2:19][CH2:20][O:21]CC1C=CC=CC=1)[CH2:8][C:9]1([C:14]([OH:16])=O)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:41]([O:48][C:49]([C@H:51]1[CH2:56][CH2:55][C@@H:54]([NH2:57])[CH2:53][CH2:52]1)=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:29])[CH:7]([CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH2:8][C:9]1([C:14](=[O:16])[NH:57][C@H:54]2[CH2:55][CH2:56][C@@H:51]([C:49]([O:48][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[O:50])[CH2:52][CH2:53]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:2])([CH3:4])[CH3:3]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 54569243HCID 54569243, compoundHCID 178427656HCID 178427656, compound

Product 1

HCID 178450995HCID 178450995, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-Benzyloxybutyl)-3-(1-carboxycyclopentyl)propanoic acid t-butyl ester (1 g, 2.48 mmole) was dissolved in ethanol (35 ml) and stirred at room temperature with 5% palladium on carbon catalyst (250 mg) under hydrogen at 50 p.s.i. (3.45 bar). After 3 hours the catalyst was removed by filtration and the solvent evaporated. The residue was dissolved in dichloromethane (40 ml) and cis-4-amino-cyclohexanecarboxylic acid benzyl ester p-toluene sulphonate salt (1.5 g, 3.70 mmole), 1-(3-dimethylaminopropyl)3-ethylcarbodiimide hydrochloride salt (1.22 g, 6.37 mmole), 1-hydroxybenzotriazole hydrate (0.97 g, 6.34 mmole) and triethylamine (1.28 g, 12.65 mmole) added. After 3 days at room temperature, the solvent was evaporated and the residue dissolved in ethyl acetate (50 ml). The solution was washed with water (50 ml), 1N hydrochloric acid (50 ml), water (50 ml) and saturated sodium hydrogen carbonate solution (50 ml), dried over magnesium sulphate and the solvent evaporated. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and pentane (1:1 by volume) and the appropriate fractions combined and evaporated to give the title product as a pale orange oil (912 mg, 61%). Found: C,70.29; H,8.94; N,2.64. C31H47NO6 requires C,70.05; H,9.08; N,2.59%.

Workup

  1. customAfter 3 hours the catalyst was removed by filtration
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in dichloromethane (40 ml)
  4. customthe solvent was evaporated
  5. dissolutionthe residue dissolved in ethyl acetate (50 ml)
  6. washThe solution was washed with water (50 ml), 1N hydrochloric acid (50 ml), water (50 ml) and saturated sodium hydrogen carbonate solution (50 ml)
  7. dry with materialdried over magnesium sulphate
  8. customthe solvent evaporated
  9. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and pentane (1:1 by volume)
  10. customevaporated

Sources & evidence

ORD record
ord-f3804358c57a41caa53a30375b9e030f
Source dataset
uspto-grants-1991_07
Patent number
US05030654

Reaction notes

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