Imidazole → HCID 11058855, compound

HRID 1353464Notes

Reaction equation

HRID 1353464 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:25]I.[C:27]1([CH2:33][O:34][C:35](=[O:48])[C@@H:36]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:38]O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[C:27]1([CH2:33][O:34][C:35](=[O:48])[C@@H:36]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:38][I:25])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 13970788Boc-L-Homoser-Obzl

Product 1

HCID 11058855HCID 11058855, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of PPh3 (4.19 g, 16 mmol) and imidazole (1.09 g, 16 mmol) in anhydrous CH2Cl2 (40 mL) was added slowly iodine (4.07 g, 16 mmol) at rt. After 5 min, a solution of (2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxy-butanoic acid phenylmethyl ester (4.12 g, 13.3 mmol) in CH2Cl2 (20 mL) was added at 0° C. After 2 h at rt, the reaction mixture was filtered through a short silica gel column. The filtrate was concentrated in vacuo, and the resulting residue was purified by flash chromatography (hexane-EtOAc, 95:5 to 9:1) to afford the product as light yellow oil (3.22 g, 58%). 1H NMR (CDCl3) δ 1.43 (s, 9H), 2.20 (m, 1H), 2.40 (m, 1H), 3.13 (m, 2H), 4.35 (br.s, 1H), 5.10 (br.s, 1H), 5.20 (AB, 2H), 7.30–7.40 (m, 5H). LC-MS: 420 (M++1).

Workup

  1. waitAfter 2 h at rt
  2. filtrationthe reaction mixture was filtered through a short silica gel column
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe resulting residue was purified by flash chromatography (hexane-EtOAc, 95:5 to 9:1)

Sources & evidence

ORD record
ord-745749e1c9f0412d86275905867e6920
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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