Dimethylformamide → 1-tert-Butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-naphthoylpiperazine

HRID 1598470Notes

Reaction equation

HRID 1598470 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[CH2:14][CH2:15][OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:42]=[CH:41][C:40]=1C(O)=O.CN([CH:55]=[O:56])C>CCCCCC.C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:55]([C:47]2[C:48]3[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:44]=[CH:45][CH:46]=2)=[O:56])[CH2:10][C@@H:9]1[CH2:14][CH2:15][OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 71232-Naphthoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12046236(S)-tert-butyl 2-(2-hydroxyethyl)piperazine-1-carboxylate

Product 1

HCID 129668321-tert-Butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-naphthoylpiperazine

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-tert-butoxycarbonyl-2(S)-(2-hydroxyethyl)piperazine (0.479 g, 2.08 mmol) in DMF was added EDC.HCl (0.432 g, 2.25 mmol), HOBT (0.314 g, 2.05 mmol) and naphthalene-2-carboxylic acid (0.353 g, 2.05 mmol). Triethylamine was added to pH 7. The reaction was stirred overnight at room temperature. The DMF was removed in vacuo and the residue dissolved in 1:1 methanol-tetrahydrofuran and 5% sodium hydroxide added. The reaction was stirred several hours, the solvent evaporated and the residue partitioned between ethyl acetate and 5% sodium hydroxide. The organic phase was dried over magnesium sulfate and the crude product thus obtained chromatoraphed on silica gel with 50% ethyl acetate in hexane. The title compound was obtained as a white foam.

Workup

  1. customThe DMF was removed in vacuo
  2. dissolutionthe residue dissolved in 1:1 methanol-tetrahydrofuran and 5% sodium hydroxide
  3. additionadded
  4. stirringThe reaction was stirred several hours
  5. customthe solvent evaporated
  6. customthe residue partitioned between ethyl acetate and 5% sodium hydroxide
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. customthe crude product thus obtained

Sources & evidence

ORD record
ord-89375778ce514edaa3ae8a2581becd19
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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