Triphenylphosphine → HCID 68813771, compound

HRID 2105017Notes

Reaction equation

HRID 2105017 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([C:22]1[CH:27]=[CH:26][C:25]([NH:28][CH:29]([C:63]2[CH:68]=[C:67]([CH2:69][CH3:70])[CH:66]=[C:65]([OH:71])[C:64]=2[F:72])[C:30]2[N:31]([C:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:32]=[C:33]([C:35]3[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=3[C:37]([NH2:39])=[O:38])[N:34]=2)=[CH:24][CH:23]=1)#[N:21].O[C@@H:74]1[CH2:78][CH2:77][O:76][CH2:75]1>C1COCC1>[C:20]([C:22]1[CH:27]=[CH:26][C:25]([NH:28][CH:29]([C:63]2[CH:68]=[C:67]([CH2:69][CH3:70])[CH:66]=[C:65]([O:71][C@H:74]3[CH2:78][CH2:77][O:76][CH2:75]3)[C:64]=2[F:72])[C:30]2[N:31]([C:44]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)[CH:32]=[C:33]([C:35]3[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=3[C:37]([NH2:39])=[O:38])[N:34]=2)=[CH:24][CH:23]=1)#[N:21]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 641512(-)-3-HydroxytetrahydrofuranHCID 68815490HCID 68815490, compound

Product 1

HCID 68813771HCID 68813771, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of triphenylphosphine (40.6 mg, 0.155 mmol) in 1 mL THF at 0° C., was added diethyl azidodicarboxylate (24.5 μL, 0.155 mmol), dropwise. The mixture was stirred at 0° C. for 20 min, then a solution of Intermediate 188.6 (36 mg, 0.052 mmol) and (R)-3-hydroxytetrahydrofuran (8.3 μL, 0.103 mmol) in 1 mL THF was added dropwise. The mixture was stirred at 0° C. for 15 min and at rt for 14 h, then was concentrated. The crude residue was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient) to afford 40.5 mg of Intermediate 204.1, contaminated with triphenylphosphine. LCMS (2 min gradient) RT=2.00 min, 768.25 (M+H)+.

Workup

  1. stirringThe mixture was stirred at 0° C. for 15 min and at rt for 14 h
  2. concentrationwas concentrated
  3. customThe crude residue was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-ede352187fe34b26a39e59b2c419eddf
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

Loading…