Réaction #48672

ord-d84c6867d5d949f78021d1ce8021af7c

Équation de réaction

CCOC(C)=O
ethyl acetate
CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1
((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester
C=C(c1ccccc1)c1ccccc1
1,1-diphenylethylene
O=C1CCC(=O)N1I
N-iodosuccinimide
→
CC(C)(C)OC(=O)N[C@@H](COCc1ccccc1)COC(CI)(c1ccccc1)c1ccccc1
desired compound
CC(C)(C)OC(=O)N[C@@H](COCc1ccccc1)COC(CI)(c1ccccc1)c1ccccc1
[(S)-2-benzyloxy-1-(2-iodo-1,1-diphenylethoxymethyl)-ethyl]-carbamic acid tert-butyl ester

Réactifs

CCOC(C)=O
ethyl acetate
CC(C)(C)OC(=O)N[C@H](CO)COCc1ccccc1
((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester
C=C(c1ccccc1)c1ccccc1
1,1-diphenylethylene
O=C1CCC(=O)N1I
N-iodosuccinimide

Réactifs

Aucun

Solvants

CC#N
acetonitrile

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Lavagewash with saturated aqueous sodium chloride
  2. 2
    SéchageDry (magnesium sulfate)
  3. 3
    Filtrationfilter
  4. 4
    Concentrationconcentrate
  5. 5
    AutrePurify on silica gel
  6. 6
    Lavageeluting with 0:100 to 30:70 ethyl acetate

Mode opératoire

Dissolve ((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester (1.0 g, 3.55 mmol) and 1,1-diphenylethylene (0.534 g, 2.96 mmol) in acetonitrile (20 mL). Add N-iodosuccinimide (0.800 g, 3.55 mmol) and stir at room temperature 72 hours. Pour into ethyl acetate and wash with saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate. Purify on silica gel, eluting with 0:100 to 30:70 ethyl acetate:hexanes to give the desired compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07745438B2uspto-grants-2010_06