Triphenylphosphine → Benzyl N-benzyloxycarbonylglycinate

HRID 1578533Notes

Reaction equation

HRID 1578533 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:35](OSC1C=CC=CC=1[N+]([O-])=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C1C=C(SSC2N=CC=CC=2)N=CC=1>C(Cl)Cl>[CH2:35]([O:14][C:13](=[O:15])[CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 14349BenzyloxycarbonylglycineHCID 650932,2'-Dipyridyl disulfideHCID 54253954HCID 54253954, compound

Product 1

HCID 79648Benzyl N-benzyloxycarbonylglycinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.09 g. of N-benzyloxycarbonylglycine, 2.62 g. of triphenyl phosphine, 2.61 g. of 2-nitrobenzenesulfenic acid benzyl ester, 2.20 g. of 2,2'-dipyridyl disulfide and 50 ml. of methylene chloride is stirred at room temperature for 3 hours. The reaction mixture is washed successively with water, saturated aqueous sodium bicarbonate, water, 0.1 N hydrochloric acid and water and then dried over anhydrous sodium sulfate. The solvent is distilled off. The residue is dissolved in methylene chloride. The solution is subjected to column chromatography using silica gel and eluted with methylene chloride. Distillation of the solvent from the eluate gives 2.51 g. of the desired product melting at 72°C.

Workup

  1. additionA mixture of 2.09 g
  2. washThe reaction mixture is washed successively with water, saturated aqueous sodium bicarbonate, water, 0.1 N hydrochloric acid and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent is distilled off
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washeluted with methylene chloride
  7. distillationDistillation of the solvent from the eluate
  8. customgives 2.51 g

Sources & evidence

ORD record
ord-6a08acce382e44278af9629317a06b91
Source dataset
uspto-grants-1976_02
Patent number
US03937718

Reaction notes

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