HOAt → HCID 21060090, compound

HRID 228124Notes

Reaction equation

HRID 228124 reaction equation
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:2]([C:11]([OH:13])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.CCN=C=NCCCN(C)C.CI.C1C=NC2N(O)N=NC=2C=1.[NH:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]1[N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1>CN(C=O)C>[Cl:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C@@H:2]([NH:1][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:11](=[O:13])[N:53]2[CH2:54][CH2:55][N:50]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][N:44]=3)[CH2:51][CH2:52]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 181649HOAtHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 10236463N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide methyliodideHCID 129471451-(Piperidin-2-yl)piperazine

Product 1

HCID 21060090HCID 21060090, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{(1R)-1-[(4-Chlorophenyl)methyl]-2-oxo-2-(4-(2-pyridyl)piperazinyl)ethyl}(tert-butoxy)carboxamide was prepared according to the procedure for Preparation XIX using Boc-p-Cl-D-Phe-OH (550 mg, 1.8 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide methiodide (1.1 g, 3.80 mmol), HOAT (260 mg, 1.9 mmol), DMF (15 mL), and 1-(2-piperidyl)piperazine (280 μl, 1.8 mmol) (Aldrich). The crude material was concentrated in vacuo to yield 810 mg. MS (ESI, pos. ion) m/z: 445 (M+H), (ESI, neg. ion) m/z: 443 (M−H). Calc'd for C23H29ClN4O3: 444.95.

Workup

  1. concentrationThe crude material was concentrated in vacuo
  2. customto yield 810 mg

Sources & evidence

ORD record
ord-92565239d8c54ba88df919efc21f7775
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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