Diisopropylethylamine → (S)-1-(tert-Butyloxycarbonyl)-4-(dipentylcarbamoyl)piperazine-2-carboxylic acid

HRID 2226614Notes

Reaction equation

HRID 2226614 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH2:26]([N:31]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:32](Cl)=[O:33])[CH2:27][CH2:28][CH2:29][CH3:30]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:32](=[O:33])[N:31]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22106956Dipentylcarbamyl chlorideHCID 40419053(2S)-1-[(tert-butoxy)carbonyl]piperazine-2-carboxylic acid

Product 1

HCID 53820654(S)-1-(tert-Butyloxycarbonyl)-4-(dipentylcarbamoyl)piperazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A partial solution of 1.32 g (5.74 mmole) of (S)-1-(tert-butyloxycarbonyl)piperazine-2-carboxylic acid in 25 ml of dried DMF was treated dropwise over 5 min with 1.48 g (11.47 mmole of diisopropylethyl amine at 25° under nitrogen with stirring. The clear solution which resulted was treated dropwise over 15 min with a solution of 1.26 g (5.74 mmole) of dipentylcarbamoyl chloride in 5 ml of DMF and the mixture was stirred under nitrogen at 25° for 16 hr. The solution was concentrated in vacuo and the residue was dissolved in 100 ml of dichloromethane which was extracted with 2×100 ml of 0.5M citric acid and 2×25 ml of water. Without drying, the solution was concentrated in vacuo to 1.85g (78%) of medium yellow oil which was homogeneous by the (silica gel, 1:1:1:1 ethylacetate: n-butanol: acetic acid: water, Rf =0.50).

Workup

  1. customThe clear solution which resulted
  2. stirringthe mixture was stirred under nitrogen at 25° for 16 hr
  3. concentrationThe solution was concentrated in vacuo
  4. dissolutionthe residue was dissolved in 100 ml of dichloromethane which
  5. extractionwas extracted with 2×100 ml of 0.5M citric acid and 2×25 ml of water
  6. customWithout drying
  7. concentrationthe solution was concentrated in vacuo to 1.85g (78%) of medium yellow oil which

Sources & evidence

ORD record
ord-699c6f02937442eda9dbc481a36c069f
Source dataset
uspto-grants-1994_09
Patent number
US05348955

Reaction notes

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