HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

1,2-Dichloroethane → 4-((S)-3-tert-Butoxycarbonylamino-2-{[5-(3,3-dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-propionyl)-piperazine-1-carboxylic acid ethyl ester

HRID 1908637
Notes
Print preview

Reaction equation

HRID 1908637 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[C:3](=[O:20])[CH2:4][O:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([C:17]([OH:19])=O)[CH:7]=1.[CH2:23]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34](=[O:46])[C@@H:35]([NH2:45])[CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:30][CH2:29]1)=[O:27])[CH3:24].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH2:23]([O:25][C:26]([N:28]1[CH2:29][CH2:30][N:31]([C:34](=[O:46])[C@@H:35]([NH:45][C:17]([C:8]2[CH:7]=[C:6]([O:5][CH2:4][C:3](=[O:20])[C:2]([CH3:1])([CH3:22])[CH3:21])[N:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:9]=2)=[O:19])[CH2:36][NH:37][C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[CH2:32][CH2:33]1)=[O:27])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 668548144-((S)-2-Amino-3-tert-butoxycarbonylamino-propionyl)-piperazine-1-carboxylic acid ethyl esterHCID 669199535-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 66920210
4-((S)-3-tert-Butoxycarbonylamino-2-{[5-(3,3-dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-propionyl)-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.7 g of 5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carboxylic acid and 2.0 g of 4-((S)-2-Amino-3-tert-butoxycarbonylamino-propionyl)-piperazine-1-carboxylic acid ethyl ester in 10 ml of DMF, 0.9 g of HOBT and 1.1 g of EDC was added and the reaction mixture was stirred for 2 h at RT. Then, the reaction mixture was diluted with water and extracted with DCM. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 3.8 g.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  5. additionThe fractions containing the product
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-ea53d095899d413e9f75b7dad8a35641
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598179B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes