4-Phenylbutyric Acid → HCID 21341798, compound

HRID 2185471Notes

Reaction equation

HRID 2185471 reaction equation
O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(C(C)C)CC)(C)C.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[C:38]1([CH2:44][CH2:45][CH2:46][C:47](O)=[O:48])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>ClCCl>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][N:35]([C:47](=[O:48])[CH2:46][CH2:45][CH2:44][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 47754-Phenylbutyric AcidHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

Product 1

HCID 21341798HCID 21341798, compoundYield 132.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis(2-oxo-3-oxazolidinyl)phosphinic chloride (2.33 g) and diisopropylethylamine (3.2 mL) were added to a solution of N-tert-butoxycarbonylpiperazine (1.13g) and 4-phenylbutyric acid (1.0 g) in dichloromethane (50 mL) at 0° C. After stirring at room temperature for 20 hr, the solvent was evaporated in vacuo. Ethyl acetate and 10% citric acid aqueous solution were added to the residue. The separated organic layer was washed with saturated sodium hydrogen carbonate, dried over sodium sulfate, and evaporated in vacuo to afford the titled compound (2.68 g) as a colorless solid: 1H NMR(400 MHz, CDCl3) δ 1.47(s, 9H), 1.98(t, 2H), 2.32 (t, 2H), 2.68 (t, 2H)3.34-3.59 (m, 8H), and 7.17-7.30 (m, 5H).

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionEthyl acetate and 10% citric acid aqueous solution were added to the residue
  3. washThe separated organic layer was washed with saturated sodium hydrogen carbonate
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e38ffd2c445d408cb5909e24f5c5749b
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…