1,2-Dichloroethane → 2-{4-[2-Amino-3-(4-fluorophenyl)-propionyl]-3-ethyl-piperazin-1-yl}-3-naphthalen-2-yl-propionamide HCl

HRID 720180Notes

Reaction equation

HRID 720180 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:17]([C:29](=[O:31])[NH2:30])[CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[CH2:13][CH:12]1[CH2:32][CH3:33])=[O:10])(C)(C)C.[Cl:43]CCCl>Cl.O1CCOCC1>[ClH:43].[NH2:7][CH:8]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:17]([CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[C:29]([NH2:30])=[O:31])[CH2:13][CH:12]1[CH2:32][CH3:33])=[O:10]

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 69588095[2-[4-(1-Carbamoyl-2-naphthalen-2-yl-ethyl)-2-ethyl-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 695876512-{4-[2-Amino-3-(4-fluorophenyl)-propionyl]-3-ethyl-piperazin-1-yl}-3-naphthalen-2-yl-propionamide HCl

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

[2-[4-(1-carbamoyl-2-naphthalen-2-yl-ethyl)-2-ethyl-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester, 37, (0.26 g, 0.5 mmol) is dissolved in 4M HCl in dioxane (7 mL). The reaction mixture is stirred for 60 minutes, then 1,2-dichloroethane (7 mL) is added. The solution is concentrated in vacuo to afford 0.24 g (quantitative yield) of the desired product.

Workup

  1. concentrationThe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-55383a673b714d45b3d1b7823f4a7d44
Source dataset
uspto-grants-2006_11
Patent number
US07132539B2

Reaction notes

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