Triphenylphosphine → HCID 118101202, compound

HRID 708923Notes

Reaction equation

HRID 708923 reaction equation
[F:1][C:2]1[C:3]([OH:21])=[C:4]([CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1)[CH2:5][N:6]([CH3:14])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[O:22]1[CH2:26][CH2:25][C@H:24](O)[CH2:23]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>[F:1][C:2]1[C:3]([O:21][C@@H:24]2[CH2:25][CH2:26][O:22][CH2:23]2)=[C:4]([CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1)[CH2:5][N:6]([CH3:14])[C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:12])[CH3:10]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2733227(S)-(+)-3-HydroxytetrahydrofuranHCID 5363146Diisopropyl azodicarboxylateHCID 70292396HCID 70292396, compound

Product 1

HCID 118101202HCID 118101202, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 17D (566 mg, 1.885 mmol), (S)-tetrahydrofuran-3-ol (365 mg, 4.15 mmol) and PPh3 (1088 mg, 4.15 mmol) in THF (5 mL) was added DIAD (0.822 mL, 4.15 mmol) dropwise. The reaction was stirred at 0° C. for 0.5 h and then at rt for 16 h. The mixture was concentrated and purified by prep HPLC to give 38A (700 mg, 1.890 mmol, 100% yield). MS (ESI) m/z: 371.2 (M+H)+.

Workup

  1. waitat rt for 16 h
  2. concentrationThe mixture was concentrated
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-c74caf380b6a4a19923ba403e282850a
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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