1-Hydroxybenzotriazole → 4-{2-[(Biphenyl-4-carbonyl)-amino]-acetyl}-piperazine-1-carboxylicacid tert-butyl ester

HRID 1178008Notes

Reaction equation

HRID 1178008 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:15]=[CH:14][C:13]([C:16]([NH:18][CH2:19][C:20]([OH:22])=O)=[O:17])=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:51]([N:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1)([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52]>CN(C=O)C.O>[C:54]([O:53][C:51]([N:58]1[CH2:63][CH2:62][N:61]([C:20](=[O:22])[CH2:19][NH:18][C:16]([C:13]2[CH:12]=[CH:11][C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:15][CH:14]=2)=[O:17])[CH2:60][CH2:59]1)=[O:52])([CH3:57])([CH3:55])[CH3:56]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2629432-((4-Phenylphenyl)formamido)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 311221914-{2-[(Biphenyl-4-carbonyl)-amino]-acetyl}-piperazine-1-carboxylicacid tert-butyl esterYield 37.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (2.928 g, 22.66 mmol) was added to a stirred solution of [(biphenyl-4-carbonyl)-amino]-acetic acid (2.892 g, 11.33 mmol) in DMF (30 mL). HOBT (1.835 g, 13.59 mmol) and EDCI.HCl (2.532 g, 13.59 mmol) were then added at room temperature. After 2 minutes, N-Boc-piperazine (3.381 g, 24.22 mmol) was added and the resulting mixture was stirred overnight. The reaction mixture was diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine solution, dried over sodium sulphate and concentrated in vacuo to afford 1.7 g (37.5% yield) of 4-{2-[(biphenyl-4-carbonyl)-amino]-acetyl}-piperazine-1-carboxylicacid tert-butyl ester. LC-MS purity: 82.06%

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-181c411793724ecdb0d068be326261a3
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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