Triphenylphosphine → HCID 67213544, compound

HRID 925925Notes

Reaction equation

HRID 925925 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@@H:8]([OH:11])[CH2:7][C@H:6]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:4].[CH3:22][O:23][C:24]1[C:33]([CH3:34])=[C:32]2[C:27]([C:28](O)=[CH:29][C:30]([C:35]3[S:36][CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[N:39]=3)=[N:31]2)=[CH:26][CH:25]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@@H:8]([O:11][C:28]2[C:27]3[C:32](=[C:33]([CH3:34])[C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)[N:31]=[C:30]([C:35]3[S:36][CH:37]=[C:38]([C:40]([F:41])([F:42])[F:43])[N:39]=3)[CH:29]=2)[CH2:7][C@H:6]1[C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58282620HCID 58282620, compoundHCID 178487696HCID 178487696, compound

Product 1

HCID 67213544HCID 67213544, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound 34d (2.18 g, 1.2 eq.), compound 203b (1.58 mg, 1 eq.), and PPh3-PS (polystyrene supported triphenylphosphine) (3.34 g, 2 eq.) in THF (50 mL) was added DIAD (2.1 mL, 2 eq.) under nitrogen. The reaction mixture was stirred at room temperature for 16 hrs. The mixture was filtered, and the filtrated was concentrated in vacuo and purified by chromatography on silica gel (DCM/MeOH) to yield compound 34e as a beige solid in 65% yield. MS (ESI, EI+): m/z=617 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrated was concentrated in vacuo
  3. custompurified by chromatography on silica gel (DCM/MeOH)

Sources & evidence

ORD record
ord-bb0b9f6d521345bdaac12c7845bd21a0
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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