Diisopropylethylamine → (S)-4-(benzyloxycarbonyl)-1-[N-(3-methylphenyl)-N-phenylcarbamoyl]piperazine-2-carboxylic acid

HRID 2226607Notes

Reaction equation

HRID 2226607 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C@H:13]([C:17]([OH:19])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:22]=[C:23]([N:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:28](Cl)=[O:29])[CH:24]=[CH:25][CH:26]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:28](=[O:29])[N:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([CH3:20])[CH:22]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C@H:13]([C:17]([OH:19])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514273(S)-4-(Benzyloxycarbonyl)piperazine-2-carboxylic acidHCID 18965178N-(3-methylphenyl)-N-phenylcarbamoyl chloride

Product 1

HCID 18655103(S)-4-(benzyloxycarbonyl)-1-[N-(3-methylphenyl)-N-phenylcarbamoyl]piperazine-2-carboxylic acidYield 116.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 264 mg (1 mmole) of (S)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acid, 265 mg (1.1 mmole) of N-(3-methylphenyl)-N-phenylcarbamoyl chloride, 390 mg (3 mmole) of DIEA in 5 mL of DMF was stirred for 16 hr at room temperature. The solution was concentrated in vacuo and the residure was taken up in 50 mL of CH2CL2 and washed with 2×25 mL of 1N HCl. Concentration in vacuo gave 0.55 g of an oil, which was carried on in Step C.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. washwashed with 2×25 mL of 1N HCl
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-9ba44a6887c84e05b05e2f3645a7a310
Source dataset
uspto-grants-1994_09
Patent number
US05348955

Reaction notes

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