1-Piperazinecarboxylic acid, ethyl ester → HCID 66920115, compound

HRID 1908636Notes

Reaction equation

HRID 1908636 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.[CH2:42]([O:44][C:45]([N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)=[O:46])[CH3:43]>C(Cl)Cl.O.C(Cl)CCl>[CH2:42]([O:44][C:45]([N:47]1[CH2:48][CH2:49][N:50]([C:13](=[O:15])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:51][CH2:52]1)=[O:46])[CH3:43]

Participants

8

Reactant 4

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2756240L-N-Cbz-3-N-Boc-Amino-alanine

Product 1

HCID 66920115HCID 66920115, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5 g of (S)-2-Benzyloxycarbonylamino-3-tert-butoxycarbonylamino-propionic acid, 3 g of triethylamine, 2.2 g of HOBT and 2.8 g of EDC in 50 ml of DCM, 2.3 g of piperazine-1-carboxylic acid ethyl ester was added at RT and stirred for 16 h. The reaction mixture was then diluted with water and then extracted with 300 ml of DCM. The organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution and dried over MgSO4. The solvents were removed under reduced pressure. The crude product was subjected to the next reaction step without further purification.

Workup

  1. extractionextracted with 300 ml of DCM
  2. washThe organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over MgSO4
  4. customThe solvents were removed under reduced pressure
  5. customThe crude product was subjected to the next reaction step without further purification

Sources & evidence

ORD record
ord-9048eb8642b6439caa7cd6f3dfa87e60
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

Loading…