Benzyl succinimido carbonate → Benzyl (2r)-3-(4-cyanophenoxy)-2-hydroxypropylcarbamate

HRID 411541Notes

Reaction equation

HRID 411541 reaction equation
[NH2:1][CH2:2][C@@H:3]([OH:14])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[CH2:15]([O:22][C:23](ON1C(=O)CCC1=O)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)(Cl)Cl.C(Cl)Cl>[C:10]([C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][C@H:3]([OH:14])[CH2:2][NH:1][C:23](=[O:24])[O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][CH:8]=1)#[N:11]

Participants

5

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 300720964-{[(2R)-3-Amino-2-hydroxypropyl]oxy}benzonitrile

Product 1

HCID 91135093Benzyl (2r)-3-(4-cyanophenoxy)-2-hydroxypropylcarbamateYield 100%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4{[(2R)-3-amino-2-hydroxypropyl]oxy}benzonitrile (see step (ii) above; 3.4 g, 17.7 mmol), TEA (2.69 g, 26.6 mmol) and CHCl3 (20 mL) was cooled to 0° C. before N-(benzyloxycarbonyloxy)succinimide (4.86 g, 19.5 mol) in CHCl3 (15 mL) was added slowly. The mixture was allowed to reach rt, and was stirred at that temperature overnight. The solvent was evaporated to give a residue that was dissolved in DCM. This solution was washed with water and brine and then dried (Na2SO4). Evaporation of the solvent gave 5.79 g (100%) of the sub-title compound.

Workup

  1. additionwas added slowly
  2. customto reach rt
  3. customThe solvent was evaporated
  4. customto give a residue that
  5. washThis solution was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9df57f2bfb3e467fbbe6b80865b95060
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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