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Benzyl Bromide → (S)-benzyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(tert-butoxycarbonylamino)propanoate

HRID 388904
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 388904
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][C:21]#[CH:22])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[N-:36]=[N+:37]=[N-:38].[Na+].[CH:40]1[CH:45]=[CH:44][C:43]([CH2:46]Br)=[CH:42][CH:41]=1>CN(C=O)C.O.O.CCOC(C)=O>[CH2:46]([N:36]1[CH:22]=[C:21]([CH2:20][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[N:38]=[N:37]1)[C:43]1[CH:44]=[CH:45][CH:40]=[CH:41][CH:42]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 7498Benzyl BromideHCID 33557Sodium Azide2×HCID 23667548Sodium AscorbateHCID 57326824(S)-benzyl 2-(tert-butoxycarbonylamino)pent-4-ynoate

Produkt 1

HCID 59166425(S)-benzyl 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(tert-butoxycarbonylamino)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel
HCID 21962138N,N-Dimethylformamide--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a mixture of (S)-benzyl 2-(tert-butoxycarbonylamino)pent-4-ynoate (0.50 g, 1.65 mmol), sodium ascorbate (0.036 g, 0.18 mmol), CuSO4-5H2O (0.022 g, 0.09 mmol) and NaN3 (0.13 g, 2.1 mmol) in DMF-H2O (5 mL, 4:1) at rt was added BnBr (0.24 mL, 2.02 mmol) and the mixture was warmed to 65° C. After 5 h LC-MS indicated low conversion. A further portion of NaN3 (100 mg) was added and heating was continued for 12 h. The reaction was poured into EtOAc and H2O and shaken. The layers were separated and the aqueous layer extracted 3× with EtOAc and the combined organic phases washed (H2O×3, brine), dried (Na2SO4), filtered, and concentrated. The residue was purified by flash (BIOTAGE®, 40+M 0-5% MeOH in CH2Cl2; TLC 3% MeOH in CH2Cl2) to afford a light yellow oil which solidified on standing (748.3 mg, 104%). The NMR was consistent with the desired product but suggests the presence of DMF. The material was used as is without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.84 (s, 1H), 7.27-7.32 (m, 10H), 5.54 (s, 2H), 5.07 (s, 2H), 4.25 (m, 1H), 3.16 (dd, J=1.0, 5.3 Hz, 1H), 3.06 (dd, J=5.3, 14.7 Hz), 2.96 (dd, J=9.1, 14.7 Hz, 1H), 1.31 (s, 9H). LC-MS: Anal. Calcd. for C24H28N4O4: 436. found: 437 (M+H)+.

Aufarbeitung

  1. temperatureheating
  2. waitwas continued for 12 h
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted 3× with EtOAc
  5. washthe combined organic phases washed (H2O×3, brine)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash (BIOTAGE®, 40+M 0-5% MeOH in CH2Cl2; TLC 3% MeOH in CH2Cl2)
  10. customto afford a light yellow oil which

Quellen und Nachweise

ORD-Eintrag
ord-a42106908b4e4af3934a7e27fcbb2fcf
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08377980B2

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