Triethylamine → HCID 69110241, compound

HRID 1359480Notes

Reaction equation

HRID 1359480 reaction equation
[NH2:1][C:2]1([C:20]([OH:22])=[O:21])[CH2:7][CH2:6][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:30](=O)([O:46]N1C(=O)CCC1=O)[O:31][CH2:32][CH:33]1[C:45]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[C:39]2[C:34]1=[CH:35][CH:36]=[CH:37][CH:38]=2>C(#N)C.O>[C:30]([CH:7]1[CH2:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:4][CH2:3][C:2]1([NH2:1])[C:20]([OH:22])=[O:21])([O:31][CH2:32][CH:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:40]2[C:45]1=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:46]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide2×HCID 22145251HCID 22145251, compound

Product 1

HCID 69110241HCID 69110241, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

A mixture of crude 1-amino-4,4-diphenylcyclohexane-1-carboxylic acid (510 mg, 1.73 mmole), triethylamine (0.37 ml, 2.65 mmole), 9-fluorenylmethyl succinimidyl carbonate (Fmoc-OSu, 880 mg, 2.61 mmole) in acetonitrile (25 ml) and water (25 ml) was stirred at room temperature overnight. TLC analysis of the reaction indicated the presence of starting material amino acid. 9-fluorenylmethyl succinimidyl carbonate (200 mg) and acetonitrile (5 ml) were added and the mixture was stirred at room temperature for another 24 hours. The reaction mixture was concentrated in vacuo to remove most of the acetonitrile, acidified to pH˜3 with 10% aqueous citric acid solution, and the white emulsion extracted three times with ethyl acetate. The combined organic layers were washed with water, brine, dried over sodium sulfate. Filtration and concentration gave a crude oil which was purified by column chromatography (eluted with 1→4→8% methanol/methylene chloride) to give Fmoc-1-amino-4,4-diphenylcyclohexane-1-carboxylic acid (350 mg, 39% yield) as a white solid, HRMS (FAB): C34H32NO4 (M+H) calc. 518.2331; observed: 518.231

Workup

  1. stirringthe mixture was stirred at room temperature for another 24 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove most of the acetonitrile
  4. extractionthe white emulsion extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and concentration
  8. customgave a crude oil which
  9. customwas purified by column chromatography (eluted with 1→4→8% methanol/methylene chloride)

Sources & evidence

ORD record
ord-e06d7d09323c482d8571abeabaa34d46
Source dataset
uspto-grants-2003_07
Patent number
US06600015B2

Reaction notes

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