1,2-Dichloroethane → HCID 23587438, compound

HRID 489679Notes

Reaction equation

HRID 489679 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[NH:15]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@@H:16]([C:24](O)=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][N:12]([C:24](=[O:25])[C@H:16]([NH:15][C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 5447384-(2-Methoxyphenyl)piperidineHCID 637610Boc-D-phenylalanine

Product 1

HCID 23587438HCID 23587438, compoundYield 81,435.5%

Procedure

The title compound was prepared according to the procedure described in Example 1 (Step f) using 4-(2-methoxyphenyl)piperidine (Maybridge) (2.68 g, 0.014 mol), Boc-D-PheOH (Advanced ChemTech) (3.71 g, 0.014 mmol), HOAT (Aldrich) (1.9 g, 0.014 mol) and EDC (Advanced ChemTech) (4.02 g, 0.021 mol). Purification by silica gel chromatography (1:1 EtOAc:hexane) provided the title compound as a colorless oil (5.0 g). MS (ESI, pos. ion) m/z: 439 (M+1). Calc'd for C26H34N2O4: 438.56.

Workup

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

Sources & evidence

ORD record
ord-677b8bb9366c40e2b254279c5ef6b2a1
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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