Diisopropylethylamine → HCID 22850667, compound

HRID 2226028

Reaction equation

HRID 2226028 reaction equation
Br.[Cl:2][C:3]1[CH:4]=[C:5]([N:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@H:13]2[C:18]([OH:20])=[O:19])=[O:11])[CH:6]=[CH:7][CH:8]=1.C(N(CC)C(C)C)(C)C.[CH2:36]([N:41]([CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:42](Cl)=[O:43])[CH2:37][CH2:38][CH2:39][CH3:40]>C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[C:5]([N:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:42](=[O:43])[N:41]([CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:14][C@H:13]2[C:18]([OH:20])=[O:19])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22106956Dipentylcarbamyl chlorideHCID 70072107(S)-1-[N-(3-Chlorophenyl)-N-phenylcarbamoyl]-piperazine-2-carboxylic acid hydrobromide

Product 1

HCID 22850667HCID 22850667, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a suspension of 1.05 g (2.3 mmole) of (S)-1-[N-(3-chlorophenyl)-N-phenylcarbamoyl]piperazine-2carboxylic acid hydrobromide (from Step C) in 20 ml of methylene chloride was added 1.23 g (9.5 mmole) of N,N-diisopropylethylamine followed by the dropwise addition of a solution of 523 mg (2.38 mmole) of dipentylcarbamoyl chloride (from Example 1, Step C-2) in 5 ml of methylene chloride. After stirring 24 hours at 25° C., the solution was extracted with 2N HCl, then H2O and dried over MgSO4. The dried methylene chloride solution was concentrated in vacuo and the residue was dissolved in isopropyl ether and was diluted with petroleum ether (bp. 30°-60° C.) until cloudy. The oil which precipitated was then decanted, redissolved in isopropanol and concentrated in vacuo to yield 464 mg (36%) of (S)-1-[N-(3-chlorophenyl)-N-phenylcarbamoyl]-4-(dipentylcarbamoyl)piperazine-2-carboxylic acid as a glassy solid; TLC showed a single spot, Rf 0.75 (Analtech SGF plates developed with isoamyl alcohol:acetone:water [5:2:1]).

Workup

  1. extractionthe solution was extracted with 2N HCl
  2. dry with materialH2O and dried over MgSO4
  3. concentrationThe dried methylene chloride solution was concentrated in vacuo
  4. dissolutionthe residue was dissolved in isopropyl ether
  5. additionwas diluted with petroleum ether (bp. 30°-60° C.) until cloudy
  6. customThe oil which precipitated
  7. customwas then decanted
  8. dissolutionredissolved in isopropanol
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b56df5c8094549138867aeabe3ae0a7c
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Linked notes

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