Triphenylphosphine → Methyl 2-(5-(tert-butoxycarbonylamino)pentyloxy)-4-fluorobenzoate

HRID 1019829Notes

Reaction equation

HRID 1019829 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([OH:31])[CH:22]=1.O[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:41]([O:40][C:39]([NH:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][O:31][C:23]1[CH:22]=[C:21]([F:20])[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26])=[O:45])([CH3:44])([CH3:43])[CH3:42]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2775386Methyl 4-fluorosalicylateHCID 44561365-(Boc-amino)-1-pentanol

Product 1

HCID 67448370Methyl 2-(5-(tert-butoxycarbonylamino)pentyloxy)-4-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was carried out under N2 atmosphere. Triphenyl phosphine (0.52 mol) was added to a solution of methyl 4-fluoro-2-hydroxybenzoate (0.47 mol), tert-butyl 5-hydroxypentylcarbamate (0.47 mol) and diisopropyl azodicarboxylate (DIAD; 0.94 mol) in THF (1 l) dropwise at −20° C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 2 h. The resulting mixture was used directly in the next step without further purification.

Workup

  1. customThe resulting mixture was used directly in the next step without further purification

Sources & evidence

ORD record
ord-fd80c91715fe4bbeb99bef8656c02dca
Source dataset
uspto-grants-2014_05
Patent number
US08716293B2

Reaction notes

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