Dicyclohexylcarbodiimide → HCID 59401188, Verbindung

HRID 76971

Reaktionsgleichung

Reaktionsgleichung von HRID 76971
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47](O)[CH2:46]2>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:10]([O:12][C@@H:47]1[CH:48]2[CH2:51][CH2:52][N:45]([CH2:50][CH2:49]2)[CH2:46]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 914043-Quinuclidinol, (-)-

Produkt 1

HCID 59401188HCID 59401188, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (1.03 g, 3.81 mmol) in THF (70 mL), are added DCC (1.03 g, 4.91 mmol), HOBt (660 mg, 4.90 mmol) and 3(R)-quinuclidinol (1.18 g, 9.48 mmol) and the resulting mixture is stirred for 12 hours at RT under nitrogen flowstream (LC-MS monitoring: complete conversion). The solvent is evaporated and the residue is partitioned between EtOAc (100 mL) and 2M K2CO3 (50 mL); the organic layer is separated, washed with brine and dried over Na2SO4. The resulting crude is purified by flash chromatography (DCM/MeOH=95/5, 0.1% NH3 (aq.)) to obtain 1.12 g of I19 (80% yield).

Aufarbeitung

  1. customThe solvent is evaporated
  2. customthe residue is partitioned between EtOAc (100 mL) and 2M K2CO3 (50 mL)
  3. customthe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customThe resulting crude is purified by flash chromatography (DCM/MeOH=95/5, 0.1% NH3 (aq.))
  7. customto obtain 1.12 g of I19 (80% yield)

Quellen und Nachweise

ORD-Eintrag
ord-0857f016133b479ea8a06b8bbeb5fae3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835682B2

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