Triphenylphosphine → HCID 66780320, compound

HRID 1958051Notes

Reaction equation

HRID 1958051 reaction equation
[N:1]([CH2:4][C:5]([N:7]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=1[CH3:29])[C:8]1[N:9]=[C:10]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[S:11][C:12]=1[C:13]#[N:14])=O)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])(O)=[O:50].[Na+].CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>O1CCCC1.O.C(Cl)Cl>[NH2:1][CH2:4][C:5]1[N:7]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=2[CH3:29])[C:8]2[N:9]=[C:10]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[S:11][C:12]=2[C:13](=[O:50])[N:14]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 86662600HCID 86662600, compound

Product 1

HCID 66780320HCID 66780320, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-azido-N-[(3-chloro-2-methylphenyl)methyl]-N-[5-cyano-2-(4-morpholinyl)-1,3-thiazol-4-yl]acetamide (300 mg, 0.695 mmol) in Tetrahydrofuran (THF) (20 mL) and H2O (2 mL) was added Ph3P (547 mg, 2.084 mmol). The mixture was stirred at rt for 5 hr before removal of the solvent. To the residue was added 50 mL DCM and 20 mL NaHCO3 (sat.), followed by Boc2O (0.323 mL, 1.389 mmol). The mixture was stirred at rt for 17 hrs. The organic layer was concentrated and purified on a silica column to give the titled compound 150 mg. (43%) LC/MS (ES) m/z=505.9 (M+H).

Workup

  1. stirringThe mixture was stirred at rt for 17 hrs
  2. concentrationThe organic layer was concentrated
  3. custompurified on a silica column

Sources & evidence

ORD record
ord-f0a3d1a7516f46b98b3e6030cb022e7d
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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