Triphenylphosphine → HCID 68714558, compound

HRID 1911517Notes

Reaction equation

HRID 1911517 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.[O:21]1[CH2:26][CH2:25][CH:24](O)[CH2:23][CH2:22]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:20])[CH:4]([NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH:24]2[CH2:25][CH2:26][O:21][CH2:22][CH2:23]2)[CH:6]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 97268Di-tert-butyl azodicarboxylateHCID 14760837HCID 14760837, compound

Product 1

HCID 68714558HCID 68714558, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (RS)-tert-butoxycarbonylamino-(3-hydroxy-phenyl)-acetic acid methyl ester (CAS 526217-60-7) in THF (10 ml) was treated under an argon atmosphere with tetrahydro-pyran-4-ol (0.24 ml), triphenylphosphine (649 mg) and di-tert-butyl azodicarboxylate (570 mg) and stirred at r.t. overnight. The reaction mixture was concentrated. The crude product was purified by column chromatography (silical gel; gradient: cyclohexane ->cyclohexane/EtOAc 1:1) to give (RS)-tert-butoxycarbonylamino-[3-(tetrahydro-pyran-4-yloxy)-phenyl]-acetic acid methyl ester (884 mg, 82%) as viscous light yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe crude product was purified by column chromatography (silical gel; gradient: cyclohexane ->cyclohexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-375fcedcff3344e6aabf92991904c2c0
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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