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

Triphenylphosphine → HCID 58505712, compound

HRID 1917602
Notes
Print preview

Reaction equation

HRID 1917602 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([OH:19])[CH:16]=[CH:17]3)=[C:12]([C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:11]=2[CH2:26][C:27]([CH3:34])([CH3:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:9])=[CH:4][CH:3]=1.[CH3:35][O:36][C:37]1[N:42]=[C:41]([CH2:43]O)[CH:40]=[CH:39][CH:38]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[N:18]3[C:13]([CH:14]=[C:15]([O:19][CH2:43][C:41]4[CH:40]=[CH:39][CH:38]=[C:37]([O:36][CH3:35])[N:42]=4)[CH:16]=[CH:17]3)=[C:12]([C:20](=[O:25])[C:21]([CH3:23])([CH3:24])[CH3:22])[C:11]=2[CH2:26][C:27]([CH3:33])([CH3:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:9])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 12325389(6-Methoxypyridin-2-yl)methanolHCID 178471307HCID 178471307, compound

Product 1

HCID 58505712HCID 58505712, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
23 °C

Procedure

To a cold (0° C.) solution of ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(2,2-dimethylpropanoyl)-7-hydroxyindolizin-2-yl}-2,2-dimethylpropanoate (100 mg, 0.21 mmol), (6-methoxy-pyridin-2-yl)-methanol (35 mg, 0.25 mmol), and triphenylphosphine (65 mg, 0.25 mmol) in THF (5 mL) is added DIAD (48 μL, 0.25 mmol). The reaction is allowed to gradually warm to 23° C. and then stirred overnight. Silica gel is added and the mixture is concentrated in vacuo then purified by flash chromatography (SiO2, hexanes to 15% EtOAc in hexanes) to give ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(2,2-dimethylpropanoyl)-7-[(6-methoxypyridin-2-yl)methoxy]indolizin-2-yl}-2,2-dimethylpropanoate (20 mg, 16%).

Workup

  1. additionSilica gel is added
  2. concentrationthe mixture is concentrated in vacuo
  3. customthen purified by flash chromatography (SiO2, hexanes to 15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0dfff31ea4be4c95b9d3fb11e5b6018d
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08618300B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes