Hydrochloric Acid → (2R)-2-Amino-3-(4-chlorophenyl)-1-[4-(2-nitrophenyl)piperazinyl]propan-1-one

HRID 1242731Notes

Reaction equation

HRID 1242731 reaction equation
Cl.[NH2:2][C@H:3]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])[CH2:8][CH2:7]1)=[O:5].ClC1C=CC(C[C@@H](NC(OC(C)(C)C)=O)C(N2CCN(C3C=CC=CC=3[N+]([O-])=O)CC2)=O)=CC=1.Cl>CCOC(C)=O>[NH2:2][C@H:3]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])[CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21060087n-{(1r)-1-[(4-Chlorophenyl)methyl]-2-[4-(2-nitrophenyl)piperazinyl]-2-oxoethyl}(tert-butoxy)-carboxamideHCID 69080220(2R)-2-amino-3-(4-chlorophenyl)-1-[4-(2-nitrophenyl)piperazinyl]propan-1-one hydrochloride

Product 1

HCID 58714294(2R)-2-Amino-3-(4-chlorophenyl)-1-[4-(2-nitrophenyl)piperazinyl]propan-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using the procedure described for the synthesis of Preparation XVI, (2R)-2-amino-3-(4-chlorophenyl)-1-[4-(2-nitrophenyl)piperazinyl]propan-1-one hydrochloride was prepared from N-{(1R)-1-[(4-chlorophenyl)methyl]-2-[4-(2-nitrophenyl)piperazinyl]-2-oxoethyl}(tert-butoxy)carboxamide (660 mg, 1.4 mmol) and a satd soln of HCl in EtOAc (10 mL). The yellow solid was filtered to give the target compound isolated as the HCl salt, as a white solid (530 mg). MS (ESI, pos. ion) m/z: 389 (M+H). Calc'd for C19H12ClN4O5: 388.13.

Workup

  1. filtrationThe yellow solid was filtered
  2. customto give the target compound

Sources & evidence

ORD record
ord-47d0571d5b534dec999d959c29faa424
Source dataset
uspto-grants-2006_10
Patent number
US07115607B2

Reaction notes

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