1,2-Dichloroethane → HCID 86693040, compound

HRID 2173426Notes

Reaction equation

HRID 2173426 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N:14]1([C:19]2[CH:20]=[C:21]([CH2:25][C:26](O)=[O:27])[CH:22]=[CH:23][CH:24]=2)[CH:18]=[N:17][N:16]=[N:15]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[Cl-].[Na+].O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:14]1([C:19]2[CH:20]=[C:21]([CH2:25][C:26]([N:11]3[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]3)=[O:27])[CH:22]=[CH:23][CH:24]=2)[CH:18]=[N:17][N:16]=[N:15]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 60757901HCID 60757901, compoundHCID 129703874Sodium hydrogencarbonate brine

Product 1

HCID 86693040HCID 86693040, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BOC-piperazine (502 mg, 2.69 mmol) was stirred in DCM (10 ml) and added the [3-(1H-tetrazol-1yl)phenyl]acetic acid (500 mg, 2.449 mmol) followed by HOBT (562 mg, 3.67 mmol) and EDC (939 mg, 4.90 mmol). The reaction was stirred at RT for 1 hr. The reaction was then poured into brine/NaHCO3 mixture and extracted with DCM. The organic layer was washed with 1 N HCl then dried over NaSO4, filtered and concentrated. The residue was purified by MPLC with 40 g ISCO Redi-sep column and eluted with 5% MeOH: 95% DCM solvent system to yield tert-butyl 4-{[3-(1H-tetrazol-1yl)phenyl]acetyl}piperazine-1-carboxylate. LC-MS (IE, m/z): 373 [M+1]+; 1H-NMR (500 MHz, CDCl3) δ ppm 9.025 (s, 1H), 7.67 (s, 1H), 7.64 (d, J=8.1 Hz, 1H), 7.58 (t, J=8.8 Hz, 1H), 7.44 (d, J=7.6 Hz, 1H), 3.87 (s, 2H), 3.66 (t, J=5 Hz, 2H), 3.53-3.47 (m, 4H), 1.49 (s, 9H);

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with 1 N HCl
  3. dry with materialthen dried over NaSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by MPLC with 40 g ISCO Redi-sep column
  7. washeluted with 5% MeOH

Sources & evidence

ORD record
ord-146abf19bbb54df199ccfae41b200aeb
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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