1,2-Dichloroethane → [2-(4-{(2R)-2-[(tert-Butoxy)carbonylamino]-3-(4-chlorophenyl)propanoyl}piperazinyl)phenyl]-N,N-dimethylcarboxamide

HRID 228111Notes

Reaction equation

HRID 228111 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:4].[NH:18]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@@H:19]([C:28](O)=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>>[C:34]([O:33][C:31]([NH:18][C@H:19]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:28]([N:14]1[CH2:15][CH2:16][N:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:3]([N:2]([CH3:17])[CH3:1])=[O:4])[CH2:12][CH2:13]1)=[O:29])=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 28749556HCID 28749556, compound

Product 1

HCID 69071519[2-(4-{(2R)-2-[(tert-Butoxy)carbonylamino]-3-(4-chlorophenyl)propanoyl}piperazinyl)phenyl]-N,N-dimethylcarboxamide

Procedure

[2-(4-{(2R)-2-[(tert-Butoxy)carbonylamino]-3-(4-chlorophenyl)propanoyl}piperazinyl)phenyl]-N,N-dimethylcarboxamide was prepared according to the procedure described in Preparation V by using N,N-dimethyl(2-piperazinylphenyl)carboxamide (Step 3) (260 mg, 1.1 mmol), Boc-p-Cl-D-Phe-OH (Peptech Corporation) (370 mg, 1.2 mmol), HOAT (Aldrich) (151 mg, 1.11 mmol), and EDC (Aldrich Chemical Company) (430 mg, 2.2 mmol). The compound was isolated as a crude white foam (480 mg) and used in the next step without further purification. MS (ESI, pos. ion) m/z: 515 (M+H). Calc'd for C27H35ClN4O4: 515.04.

Workup

  1. customdescribed in Preparation V

Sources & evidence

ORD record
ord-2e68e18ddfaa47409b4d18a133f8ef00
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

Loading…