Imidazole → tert-butyl N-[(1R)-1-[4-(iodomethyl)-1,3-oxazol-2-yl]ethyl]carbamate

HRID 2070997Notes

Reaction equation

HRID 2070997 reaction equation
[I:1]I.N1C=CN=C1.O[CH2:9][C:10]1[N:11]=[C:12]([C@H:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:16])[O:13][CH:14]=1>C(Cl)Cl>[I:1][CH2:9][C:10]1[N:11]=[C:12]([C@H:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:16])[O:13][CH:14]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 807IodineHCID 68670262(R)-tert-butyl 1-(4-(hydroxymethyl)oxazol-2-yl)ethylcarbamate

Product 1

HCID 68670282tert-butyl N-[(1R)-1-[4-(iodomethyl)-1,3-oxazol-2-yl]ethyl]carbamateYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of TPP (873 mg, 3.33 mmol) in CH2Cl2 (10 mL), was added I2 (845 mg, 3.33 mmol), and stirred for 10 min. Imidazole (227 mg, 3.33 mmol) was added and stirred for an additional 10 min and then a solution of (R)-tert-butyl 1-(4-(hydroxymethyl)oxazol-2-yl)ethylcarbamate (537 mg, 2.22 mmol) in CH2Cl2 (15 mL) was added. After 2 h, the reaction mixture was washed successively with sat. aq. NaHCO3, aq. Na2S2O3, dried on Na2SO4 and concentrated under low pressure. The residue was chromatographed on silica gel (20% ethyl acetate/80% hexanes) to yield 84% of (R)-tert-butyl 1-(4-(iodomethyl)oxazol-2-yl)ethylcarbamate.

Workup

  1. stirringstirred for an additional 10 min
  2. waitAfter 2 h
  3. washthe reaction mixture was washed successively with sat. aq. NaHCO3, aq. Na2S2O3
  4. customdried on Na2SO4
  5. concentrationconcentrated under low pressure
  6. customThe residue was chromatographed on silica gel (20% ethyl acetate/80% hexanes)

Sources & evidence

ORD record
ord-828b64a114824c14aa99835590cde541
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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