1,2-Dichloroethane → HCID 23587432, compound

HRID 489695Notes

Reaction equation

HRID 489695 reaction equation
Cl.[CH:2]1[C:14]2[CH:13]([CH2:15][O:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.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>[Cl:50][C:47]1[CH:48]=[CH:49][C:44]([CH2:43][C@@H:42]([NH:41][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[C:51]([N:29]2[CH2:28][CH2:27][CH:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[NH:19][C:17]([O:16][CH2:15][CH:13]3[C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[C:6]4[C:14]3=[CH:2][CH:3]=[CH:4][CH:5]=4)=[O:18])[CH2:31][CH2:30]2)=[O:52])=[CH:45][CH:46]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 131725246HCID 131725246, compound

Product 1

HCID 23587432HCID 23587432, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the procedure described in Example 1 (Step f) from (fluoren-9-ylmethoxy)-N-(2-(4-piperidyl)phenyl)-carboxamide hydrochloride (Step b) (6.51 g, 15 mmol), DIEA (2.7 mL, 15 mmol), Boc-p-Cl-D-PheOH (PepTech Corporation) (6.8 g, 22.5 mmol), HOAT (Aldrich) (3.1 g, 22.5 mmol) and EDC (Aldrich) (4.32 g, 22.5 mmol) in DMF (25 mL). Purification by silica gel chromatography (3:1 hexane:EtOAc) provided the title compound as a white foam (6.87 g). MS (ESI, pos. ion) m/z: 680 (M+1); MS (ESI, neg. ion) m/z: 678 (M−1). Calc'd for C40H42ClN3O5: 679.28.

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography (3:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-d49326748130451386a809c852b2d19d
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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