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Benzyl 4-Hydroxybenzoate → benzyl (S)-4-(2-amino-1-propoxy)benzoate

HRID 354502
Notes
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Reaction equation

HRID 354502 reaction equation
C(OC([NH:8][C@@H:9]([CH3:12])[CH2:10][OH:11])=O)(C)(C)C.O[C:14]1[CH:29]=[CH:28][C:17]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[CH:16][CH:15]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[NH2:8][C@@H:9]([CH3:12])[CH2:10][O:11][C:14]1[CH:29]=[CH:28][C:17]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[CH:16][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7180Benzyl 4-HydroxybenzoateHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 86587801benzyl (S)-4-(2-amino-1-propoxy)benzoateYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (0° C.) solution of (S)-2-(N-tert-butoxycarbonylamino)-1-propanol (6.74 g, 0.04 mol), benzyl 4-hydroxybenzoate (8.78 g, 0.04 mol), and Ph3P (15.13 g, 0.06 mol) in THF (100 mL) was added diisopropyl azodicarboxylate (DIAD) (11.4 mL, 0.06 mol), and the resulting mixture was heated under reflux overnight. The solution was evaporated and the residue was dissolved in CH2Cl2 (30 mL) and TFA (30 mL). The resulting solution was stirred at room temp for 30 min., and the solution was evaporated in vacuo. The residue was dissolved in CHCl3, washed with sat. NaHCO3, dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica-gel with CHCl3 to CHCl3:MeOH (9:1, v/v) as eluent to give 6.63 g (2 steps, 60%) benzyl (S)-4-(2-amino-1-propoxy)benzoate as a yellow oil. 1H-NMR (CDCl3) δ1.18 (d, J=6.3 Hz, 3 H), 3.35-3.39 (m, 1 H), 3.71-3.75 (m, 1 H), 3.90-3.93 (m, 1 H), 5.34 (s, 2 H), 6.90-6.93 (m, 2 H), 7.32-7.46 (m, 5 H), 8.01-8.04 (m, 2 H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux overnight
  3. customThe solution was evaporated
  4. dissolutionthe residue was dissolved in CH2Cl2 (30 mL)
  5. stirringThe resulting solution was stirred at room temp for 30 min.
  6. customthe solution was evaporated in vacuo
  7. dissolutionThe residue was dissolved in CHCl3
  8. washwashed with sat. NaHCO3
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. customThe residue was purified by column chromatography on silica-gel with CHCl3 to CHCl3:MeOH (9:1

Sources & evidence

ORD record
ord-9a5647b7270a41998c6b3373354638cb
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06756378B2

Reaction notes

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