Triphenylphosphine → 3,5-Dichloro-2-hydroxy-4-(4-tert-butoxycarbonylmethylaminobutoxy)benzoic acid methyl ester

HRID 2229814Notes

Reaction equation

HRID 2229814 reaction equation
[C:1]([O:5][C:6]([CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][C:17](=[O:28])[C:18]1[CH:23]=[C:22]([Cl:24])[C:21](O)=[C:20]([Cl:26])[C:19]=1[OH:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:15][O:16][C:17](=[O:28])[C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:20]([Cl:26])[C:19]=1[OH:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 108458284-Tert-butoxycarbonylmethylamino-1-butanolHCID 15489807Methyl 3,5-dichloro-2,4-dihydroxybenzoate

Product 1

HCID 543192833,5-Dichloro-2-hydroxy-4-(4-tert-butoxycarbonylmethylaminobutoxy)benzoic acid methyl esterYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-tert-butoxycarbonylmethylamino-1-butanol (3 g) and known 3,5-dichloro-2,4-dihydroxybenzoic acid methyl ester (3.85 g) in THF (80 ml) were added triphenylphosphine (4.26 g) and diisopropyl azodicarboxylate (3.2 ml) under ice-cooling, and the mixture was stirred for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1 v/v) to give the title compound (5.2 g, yield 83%).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1 v/v)

Sources & evidence

ORD record
ord-c87f8d0962944403ae905f1f035bc7b9
Source dataset
uspto-grants-2002_07
Patent number
US06420561B1

Reaction notes

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