1,2-Dichloroethane → {2-(4-Hydroxy-phenyl)-1-[1-methylcarbamoyl-2-(4-nitro-phenyl)-ethylcarbamoyl]-ethyl} carbamic acid tert-butyl ester

HRID 500101

Reaktionsgleichung

Reaktionsgleichung von HRID 500101
[CH:1]([N:4](C(C)C)CC)(C)[CH3:2].C(Cl)CCl.[CH:14]1[CH:15]=[CH:16][C:17]2[N:22]([OH:23])N=N[C:18]=2[CH:19]=1.[OH2:24].[NH:25]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:26]([C:35]([OH:37])=O)[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1.[CH3:45][N:46]([CH:48]=[O:49])C>>[C:41]([O:40][C:38](=[O:39])[NH:25][CH:26]([C:35](=[O:37])[NH:4][CH:1]([C:48](=[O:49])[NH:46][CH3:45])[CH2:2][C:14]1[CH:15]=[CH:16][C:17]([N+:22]([O-:23])=[O:24])=[CH:18][CH:19]=1)[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=1)([CH3:44])([CH3:43])[CH3:42]

Komponenten

7

Edukt 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-

Produkt 1

HCID 68657947{2-(4-Hydroxy-phenyl)-1-[1-methylcarbamoyl-2-(4-nitro-phenyl)-ethylcarbamoyl]-ethyl} carbamic acid tert-butyl ester

Versuchsvorschrift

H-L-Phe(4-NO2)—NMe (200 mg, 0.770 mmol) is dissolved in 1 mL DMF. Diisopropylethylamine (209 mg, 1.62 mmol), EDC (162 mg, 0.847 mmol), HOBt.H2O (130 mg, 0.847 mmol), and Boc-Tyr (238 mg, 0.847 mmol) are added and the mixture is stirred for 18 hr. at 20° C. The mixture is partitioned between water and EtOAc (2×60 mL). The organics are combined and washed with brine, dried over MgSO4, filtered and evaporated to give crude product. Purification by flash chromatography, which is eluted with 97:3 DCM:methanol to give pure white solid.

Aufarbeitung

  1. customat 20° C
  2. customThe mixture is partitioned between water and EtOAc (2×60 mL)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude product
  8. customPurification by flash chromatography, which
  9. washis eluted with 97:3 DCM
  10. custommethanol to give pure white solid

Quellen und Nachweise

ORD-Eintrag
ord-08d5b3304b664301be4a5410300acdb9
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07769575B2

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