Triphenylphosphine → (R)-N-(tert-butoxycarbonyl)-2-(5-benzyloxy-2-bromophenoxy)-1-(4-benzyloxyphenyl)ethylamine

HRID 1582808Notes

Reaction equation

HRID 1582808 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]([O:19][C:20]([NH:22][C@H:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:28][CH:27]=1)[CH2:24][OH:25])=[O:21])([CH3:18])([CH3:17])[CH3:16].[CH2:40]([O:47][C:48]1[CH:49]=[CH:50][C:51]([Br:55])=[C:52](O)[CH:53]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[C:15]([O:19][C:20]([NH:22][C@H:23]([C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:30][CH:31]=1)[CH2:24][O:25][C:50]1[CH:49]=[C:48]([O:47][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:53]=[CH:52][C:51]=1[Br:55])=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylate2×HCID 227180755-(Benzyloxy)-2-bromophenolHCID 60086323(R)-2-(tert-butoxycarbonyl)amino-2-(4-benzyloxyphenyl)ethanol

Product 1

HCID 60086347(R)-N-(tert-butoxycarbonyl)-2-(5-benzyloxy-2-bromophenoxy)-1-(4-benzyloxyphenyl)ethylamineYield 75.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazodicarboxylate (0.10 ml, 0.603 mmol) was added to (R)-2-(tert-butoxycarbonyl)amino-2-(4-benzyloxyphenyl)ethanol (161 mg, 0.469 mmol), 5-benzyloxy-2-bromophenol (131 mg, 0.469 mmol) and triphenylphosphine (160 mg, 0.610 mmol) in tetrahydrofuran (3 ml) under a nitrogen stream, followed by stirring for 5 hours at room temperature. Diisopropylazodicarboxylate (0.05 ml, 0.302 mmol) was added to the reaction mixture followed by stirring for 3 hours at room temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4, v/v) to give (R)-N-(tert-butoxycarbonyl)-2-(5-benzyloxy-2-bromophenoxy)-1-(4-benzyloxyphenyl)ethylamine (214 mg, Yield 75%).

Workup

  1. stirringby stirring for 3 hours at room temperature
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed sequentially with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4, v/v)

Sources & evidence

ORD record
ord-a5be5bd1969c405297f13bb6ef1c002f
Source dataset
uspto-grants-2004_05
Patent number
US06737417B2

Reaction notes

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