Diisopropylethylamine → (S)[1-{(2-tert-Butoxycarbonylamino-ethyl)-[(2-methyl-2-phenyl-propylcarbamoyl)-methyl]-carbamoyl}-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester

HRID 841144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 841144
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:30][C:31]1[N:32]=[CH:33][N:34]([C:36]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:35]=1)[C:13]([N:15]([CH2:26][C:27](O)=[O:28])[CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:56][C:57]([CH3:66])([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[CH2:58][NH2:59].C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@H:12]([C:13](=[O:14])[N:15]([CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:26][C:27](=[O:28])[NH:59][CH2:58][C:57]([CH3:66])([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[CH3:56])[CH2:30][C:31]1[N:32]=[CH:33][N:34]([C:36]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:35]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 210601Phenethylamine, beta,beta-dimethyl-, hydrochlorideHCID 2724699PyBOPHCID 18717554(S)[[2-Benzyloxycarbonylamino-3-(1-trityl-1H-imidazol-4-yl)-propionyl]-(2-tert-butoxycarbonylamino-ethyl)-amino]-acetic acid

Produkt 1

HCID 70169971(S)[1-{(2-tert-Butoxycarbonylamino-ethyl)-[(2-methyl-2-phenyl-propylcarbamoyl)-methyl]-carbamoyl}-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl esterAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

The compound from Step 3 (1.3 g, 1.8 mmol) was dissolved in methylene chloride (10 mL). β,β-dimethylphenethylamine hydrochloride (Example 1, Step 6) (0.370 g, 2 mmol) was added followed by diisopropylethylamine (1 mL, 5.7 mmol) and PyBOP (1.04 g, 2 mmol) dissolved in methylene chloride (10 mL). The reaction was stirred overnight at room temperature. The solution was concentrated, the residue taken up in ethyl acetate and washed three times with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated to give a white solid; 1.09 g (70% yield). MS-APCI: M+1=863.

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. washwashed three times with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-c246135d11f942a89c483a139b50f77d
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06369034B1

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