Triethylamine → HCID 59902684, compound

HRID 2230419Notes

Reaction equation

HRID 2230419 reaction equation
[C:1]([O:4][C@@H:5]([C@H:9]([O:40][C:41](=[O:43])[CH3:42])[C@H:10]([O:36][C:37](=[O:39])[CH3:38])[C@@H:11]([NH:17][C:18](=[O:35])[C@H:19]([CH2:31][CH:32]([CH3:34])[CH3:33])[NH:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[CH2:12][O:13][C:14](=[O:16])[CH3:15])[C:6](O)=[O:7])(=[O:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:59][C@H:60]([C:67]1[CH:72]=[CH:71][C:70]([CH3:73])=[CH:69][CH:68]=1)[CH2:61][C:62]([O:64][CH2:65][CH3:66])=[O:63].C(N(CC)CC)C>C(#N)C>[C:1]([O:4][C@@H:5]([C@H:9]([O:40][C:41](=[O:43])[CH3:42])[C@H:10]([O:36][C:37](=[O:39])[CH3:38])[C@@H:11]([NH:17][C:18](=[O:35])[C@H:19]([CH2:31][CH:32]([CH3:34])[CH3:33])[NH:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[CH2:12][O:13][C:14](=[O:16])[CH3:15])[C:6]([NH:59][C@H:60]([C:67]1[CH:68]=[CH:69][C:70]([CH3:73])=[CH:71][CH:72]=1)[CH2:61][C:62]([O:64][CH2:65][CH3:66])=[O:63])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 679231HCID 679231, compoundHCID 59902680HCID 59902680, compound

Product 1

HCID 59902684HCID 59902684, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of [(2S,3R,4R,5S)-2,3,4,6-tetraacetoxy-5-(N-benzyloxycarbonyl-L-leucyl)aminohexanoic acid (250 mg) in acetonitrile (10 ml) were added N-hydroxy-5-norbornene-2,3-dicarboxyimide (110 mg) and N,N′-dicyclohexylcarbodimide (110 mg) and the mixture was stirred at room temperature for 1 hour. After addition of a solution of ethyl (S)-3-amino-3-(4-methylphenyl)propionate (150 mg) and triethylamine (0.13 ml) in acetonitrile (10 ml), the whole was stirred at room temperature for 18 hours. The formed insoluble solid was filtrated off and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 ml) and washed with saturated brine (50 ml×2), followed by drying over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was passed through silica gel column chromatography, followed by elution with ethyl acetate-hexane (2:1). The effective fractions were combined and concentrated under reduced pressure to afford the title compound (184 mg).

Workup

  1. stirringthe whole was stirred at room temperature for 18 hours
  2. filtrationThe formed insoluble solid was filtrated off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  5. washwashed with saturated brine (50 ml×2)
  6. dry with materialby drying over anhydrous sodium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. washfollowed by elution with ethyl acetate-hexane (2:1)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a9fc9255bda04abd9ba4a177cdbe91e5
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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