Triphenylphosphine → HCID 89590849, compound

HRID 522408Notes

Reaction equation

HRID 522408 reaction equation
[CH3:1][C:2]1([C@H:8]2[C:35](=[O:36])[N:34]3[CH2:37][C@@H:31]([CH2:32][C@H:33]3[C:38]([O:40][CH3:41])=[O:39])[O:30][C:20]3=[N:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[C:28]([OH:29])=[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[CH2:42][C@H:12]3[O:11][C:10](=[O:43])[NH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:64]1[CH2:69][CH2:68][N:67]([CH3:70])[CH2:66][CH2:65]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][C:2]1([C@H:8]2[C:35](=[O:36])[N:34]3[CH2:37][C@@H:31]([CH2:32][C@H:33]3[C:38]([O:40][CH3:41])=[O:39])[O:30][C:20]3=[N:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[C:28]([O:29][CH:64]4[CH2:69][CH2:68][N:67]([CH3:70])[CH2:66][CH2:65]4)=[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[CH2:42][C@H:12]3[O:11][C:10](=[O:43])[NH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 660484-Piperidinol, 1-methyl-HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178501304HCID 178501304, compound

Product 1

HCID 89590849HCID 89590849, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A reaction tube was charged with the product of step 5 (400 mg, 0.674 mmol) and triphenylphosphine (1414 mg, 5.39 mmol). The tube was sealed and THF (6737 μl) was added via syringe at 0° C. 4-hydroxy-1-methylpiperidine (633 μl, 5.39 mmol) was added followed by slow addition of diisopropyl azodicarboxylate (1044 μl, 5.39 mmol). After 5 min, the cooling bath was removed and the mixture was allowed to reach room temperature and stirred for 10 minutes. The reaction tube was heated at 40° C. LCMS showed complete reaction after 2 hours. The reaction mixture was concentrated to dryness in rotavap and the residue was purified on a gold cap silica gel (120 g) column (gradient: 0 to 50% solvent B in dichloromethane (solvent B: 20% methanol in ethyl acetate)) to give the title compound (450 mg, 0.651 mmol, 97% yield) as a white powder.

Workup

  1. customThe tube was sealed
  2. customthe cooling bath was removed
  3. customto reach room temperature
  4. customreaction after 2 hours
  5. concentrationThe reaction mixture was concentrated to dryness in rotavap
  6. customthe residue was purified on a gold
  7. customcap silica gel (120 g) column (gradient: 0 to 50% solvent B in dichloromethane (solvent B: 20% methanol in ethyl acetate))

Sources & evidence

ORD record
ord-f2bc9b4e299e4b31b0029332e51056d9
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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