Benzyl Alcohol → Benzyl N-benzyloxycarbonylglycinate

HRID 1578534Notes

Reaction equation

HRID 1578534 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.[CH2:16](O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=C(SSC2N=CC=CC=2)N=CC=1>C(Cl)Cl>[CH2:16]([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:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 14349BenzyloxycarbonylglycineHCID 650932,2'-Dipyridyl disulfide

Product 1

HCID 79648Benzyl N-benzyloxycarbonylglycinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1.05 g. of N-benzyloxycarbonylglycine, 0.54 g. of benzylalcohol and 50 ml. of methylene chloride is added dropwise a solution of 1.31 g. of triphenyl phosphine and 1.10 g. of 2,2'-dipyridyl disulfide in 20 ml. of methylene chloride while stirring at room temperature. After completion of the addition, the mixture is stirred at room temperature for an additional 6 hours. The reaction mixture is treated with the same procedure as described above to give 1.36 g. of the desired product melting at 71° - 72°C.

Workup

  1. additionTo a mixture of 1.05 g
  2. additionAfter completion of the addition
  3. additionThe reaction mixture is treated with the same procedure
  4. customto give 1.36 g

Sources & evidence

ORD record
ord-1d73d69d212945a2ba2e12f073675fcc
Source dataset
uspto-grants-1976_02
Patent number
US03937718

Reaction notes

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