1,2-Dichloroethane → HCID 69151723, compound

HRID 489682Notes

Reaction equation

HRID 489682 reaction equation
Cl.[CH3:2][S:3]([N:6]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[CH2:7][CH2:8][N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19])(=[O:5])=[O:4].CCN(C(C)C)C(C)C.[NH:41]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[C@@H:42]([C:51](O)=[O:52])[CH2:43][C:44]1[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[O:19]=[C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17](=[O:18])[N:9]1[CH2:8][CH2:7][N:6]([S:3]([CH3:2])(=[O:4])=[O:5])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]1[CH2:31][CH2:30][N:29]([C:51](=[O:52])[C@H:42]([NH:41][C:54]([O:56][C:57]([CH3:59])([CH3:58])[CH3:60])=[O:55])[CH2:43][C:44]2[CH:45]=[CH:46][C:47]([Cl:50])=[CH:48][CH:49]=2)[CH2:28][CH2:27]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 22266222HCID 22266222, compound

Product 1

HCID 69151723HCID 69151723, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the procedure described in Example 1, (Step f) from 2-(2-[(methylsulfonyl)(2-(4-piperidyl)phenyl)amino]ethyl) isoindoline-1,3-dione hydrochloride (Step b) (1.28 g, 2.8 mmol), DIEA (0.54 mL, 3.0 mmol), Boc-p-Cl-D-PheOH (PepTech Corporation) (1.36 g, 4.5 mmol), HOAT (Aldrich) (0.615 g, 4.5 mmol) and EDC (Aldrich) (0.864 g, 4.5 mmol) in DMF (15 mL). Purification by silica gel chromatography (1:1 hexane:EtOAc) provided the title compound as a white foam (1.83 g %). MS (ESI, pos. ion) m/z: 709 (M+1); MS (ESI, neg. ion) m/z: 707 (M−1). Calc'd for C36H41ClN4O7S: 708.24.

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography (1:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-83b2492067c044d78b50b79c814a707a
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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