Triphenylphosphine → Methyl 3-{4-[(tert-butoxycarbonyl)amino]butoxy}-1-(methoxymethoxy)-2-naphthoate

HRID 488681

Reaction equation

HRID 488681 reaction equation
[OH:1][C:2]1[C:3]([C:16]([O:18][CH3:19])=[O:17])=[C:4]([O:12][CH2:13][O:14][CH3:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:39]([O:43][C:44]([NH:46][CH2:47][CH2:48][CH2:49][CH2:50]O)=[O:45])([CH3:42])([CH3:41])[CH3:40].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:39]([O:43][C:44]([NH:46][CH2:47][CH2:48][CH2:49][CH2:50][O:1][C:2]1[C:3]([C:16]([O:18][CH3:19])=[O:17])=[C:4]([O:12][CH2:13][O:14][CH3:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:45])([CH3:42])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 545141tert-Butyl N-(4-hydroxybutyl)carbamateHCID 5462977Diethyl azodicarboxylateHCID 22271918HCID 22271918, compound

Product 1

HCID 22271972Methyl 3-{4-[(tert-butoxycarbonyl)amino]butoxy}-1-(methoxymethoxy)-2-naphthoateYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 3-hydroxy-1-(methoxymethoxy)-2-naphthoate (41 mg, 0.16 mmol), triphenylphosphine (41 mg, 0.16 mmol) and N-(tert-butoxycarbonyl)-4-hydroxy-1-butylamine (33 mg, 0.17 mmol) in THF (0.5 mL) was added diethylazodicarboxylate (30 μL, 0.19 mmol). The mixture was stirred at ambient temperature for 30 minutes, concentrated under reduced pressure and purified on silica gel eluting with 30% ethyl acetate/hexanes to provide the titled compound (28 mg, 41%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified on silica gel eluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2255b90bb88b40b8aaf957c537c5f008
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Linked notes

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