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

Propargyl alcohol → HCID 178458754, compound

HRID 2089047
Notes
Print preview

Reaction equation

HRID 2089047 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([OH:32])[CH:30]=3)[N:25]([S:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:24]=2)[CH:3]=1.[CH2:42](O)[C:43]#[CH:44].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CCOC(C)=O.ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([O:32][CH2:44][C:43]#[CH:42])[CH:30]=3)[N:25]([S:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:24]=2)[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 178453994HCID 178453994, compound

Product 1

HCID 178458754HCID 178458754, compoundYield 70.4%

Reagents, catalysts & solvents 3

HCID 6344
Dichloromethane
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 224a (0.075 g, 0.125 mmol), propargyl alcohol (0.018 mL, 0.313 mmol), di-tert-butyl azodicarboxylate (0.072 g, 0.313 mmol), and triphenylphosphine (3 mmol/1 g)-polymer supported (0.105 g, 0.4 mmol) in THF (3.0 mL) was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc and dichloromethane, filtered through celite, concentrated and purified on 12 g column, using Analogix System, eluted with 0-30% EtOAc in hexanes to give 56.0 mg (70%) of the title compound.

Workup

  1. filtrationfiltered through celite,
  2. concentrationconcentrated
  3. custompurified on 12 g column
  4. washeluted with 0-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-4033c011f86c494cb3f4e0dccb5e4c0f
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08435980B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes