p-Toluenesulfonic acid → Ac-Gly-Sar-OBzl

HRID 1422521

Reaktionsgleichung

Reaktionsgleichung von HRID 1422521
[NH:1]([C:6]([CH3:8])=[O:7])[CH2:2][C:3](O)=[O:4].[NH:9]([CH2:11][C:12]([O:14]CC1C=CC=CC=1)=[O:13])[CH3:10].[CH3:22][C:23]1[CH:24]=[CH:25][C:26](S(O)(=O)=O)=[CH:27][CH:28]=1.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[NH:1]([C:6]([CH3:8])=[O:7])[CH2:2][C:3]([N:9]([CH2:11][C:12]([O:14][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:13])[CH3:10])=[O:4]

Komponenten

8

Edukt 6

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 10972AcetylglycineHCID 757711-HydroxybenzotriazoleHCID 7019103Benzyl 2-(methylamino)acetate

Produkt 1

HCID 131732224Ac-Gly-Sar-OBzl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ac-Gly-OH a (4.10 g, 35.0 mmol), Sar-OBzl.PTSA b (11.71 g, 33.3 mmol), triethylamine (5.58 mL, 40.0 mmol), HOBt (1.35 g, 10 mmol) and DCC (8.25 g, 40.0 mmol) were stirred in 200 mL THF overnight. The mixture was filtered to discard DCU and removed THF in vacuum. The concentrated residue was dissolved in 100 mL ethyl acetate and washed with 100 mL 10% citric acid(aq) twice, 100 mL 5% NaHCO3(aq) twice and 100 mL brine twice, dried over MgSO4, and evaporated in vacuum to get about 9 g light yellow oily Ac-Gly-Sar-OBzl c.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customremoved THF in vacuum
  3. dissolutionThe concentrated residue was dissolved in 100 mL ethyl acetate
  4. washwashed with 100 mL 10% citric acid(aq) twice
  5. dry with material100 mL 5% NaHCO3(aq) twice and 100 mL brine twice, dried over MgSO4
  6. customevaporated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9456afc046e5498fa2a63a0f51eb0d90
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927499B2

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