1,2-Dichloroethane → HCID 23587433, compound

HRID 489675Notes

Reaction equation

HRID 489675 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14](O)[CH3:15])[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[NH:26]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@@H:27]([C:36](O)=[O:37])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1.C1C=NC2N([OH:55])N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][C@@H:27]([NH:26][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:36]([N:2]2[CH2:7][CH2:6][CH:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH2:14][CH2:15][OH:55])[CH2:4][CH2:3]2)=[O:37])=[CH:34][CH:33]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 22266192HCID 22266192, compound

Product 1

HCID 23587433HCID 23587433, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the procedure described in Example 1 (Step f) using 1-(2-(4-piperidyl)phenyl)ethan-1-ol hydrochloride (Step c) (0.72 g, 3.0 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 (5 mL). Purification by silica gel chromatography (100% EtOAc) provided the title compound as a white foam (1.09 g). MS (EST, pos. ion) m/z. 487 (M+1); MS (ESI, neg. ion) m/z: 485 (M−1). Calc'd for C27H35ClN2O4: 486.23.

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-b46fed87bce74e8b898efc4e74a62358
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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