HCID 131733559, compound → HCID 131733560, compound

HRID 1747233Notes

Reaction equation

HRID 1747233 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]([CH2:17][OH:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([I:16])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]([CH:17]=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([I:16])[CH:11]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 131733559HCID 131733559, compound

Product 1

HCID 131733560HCID 131733560, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of [(R)-1-hydroxymethyl-2-(3-iodo-phenyl)-ethyl]-carbamic acid tert-butyl ester K-9 (5.32 g, 14.1 mmol) in DCM (100 mL) was added dropwise to a RT suspension of DMP (6.78 g, 15.5 mmol) in DCM (40 mL) and the resulting mixture was stirred for 1.5 h. The reaction was quenched with 20% aq. NaHCO3 and 10% aq. Na2S2O3 and stirred for 1 h. The layers were separated and the aqueous layer was extracted with DCM (2×). The combined organic extracts were washed with 1M aq. HCl, brine, dried over Na2SO4, filtered and evaporated in vacuo. The crude product was subsequently triturated with a little DCM to give the title compound as an orange solid. LC-MS A: tR=0.87 min; [M+H]+=No ionisation.

Workup

  1. customThe reaction was quenched with 20% aq. NaHCO3 and 10% aq. Na2S2O3
  2. stirringstirred for 1 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (2×)
  5. washThe combined organic extracts were washed with 1M aq. HCl, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe crude product was subsequently triturated with a little DCM

Sources & evidence

ORD record
ord-90b17c68c88a4e46a38af69787302927
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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