n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide → (2R)-2-Amino-3-(3,4-dichlorophenyl)-1-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)propan-1-one

HRID 228083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228083
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C@@H:10]([NH:30]C(OC(C)(C)C)=O)[C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]>CCOC(C)=O>[NH2:30][C@H:10]([CH2:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[C:11]([N:13]1[CH2:14][CH2:15][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH2:17][CH2:18]1)=[O:12]

Komponenten

3

Edukt 1

HCID 21060073n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide

Produkt 1

HCID 69073248(2R)-2-Amino-3-(3,4-dichlorophenyl)-1-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(2R)-2-Amino-3-(3,4-dichlorophenyl)-1-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)propan-1-one was prepared according to the procedure for Preparation XVI using N-[(1R)-1-[(3,4-dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide (Step 1) (1.0 g, 1.8 mmol) and satd HCL in EtOAC. The resulting crude material was diluted with EtOAc and washed with satd NaHCO3 soln. The organic layer was separated, dried over Na2SO4, filtered and concentrated in vacuo (700 mg). MS (ESI, pos. ion) m/z: 471 (M+H), (ESI, neg. ion) m/z: 469 (M−H). Calc'd for C20H24Cl2N4O3S: 470.09. Anal. Calc'd for C20H24Cl2N4O3S: C, 50.96; H, 5.13; N, 11.88; Cl, 15.04. Found C, 50.66; H, 5.14; N, 11.51; Cl, 15.11.

Aufarbeitung

  1. washwashed with satd NaHCO3 soln
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo (700 mg)

Quellen und Nachweise

ORD-Eintrag
ord-b958b057b71148e09dda40cd7a9602d8
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560460B2

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