Sodium Iodide → Isopropyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate

HRID 706367Notes

Reaction equation

HRID 706367 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:16]OS(C)(=O)=O)[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-:22].[Na+]>CC(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:16][I:22])[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 89815000isopropyl N-(tert-butoxycarbonyl)-O-(methylsulfonyl)serinate

Product 1

HCID 89816165Isopropyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoateYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2 (392 g) in acetone (3.14 L), sodium iodide (542 g) was added. The reaction temperature went up to 29° C. from 17° C. The reaction mixture was maintained at room temperature over weekend. The mixture was filtrated and washed with MTBE. The filtrate and washings were combined and concentrated. The residue was treated with MTBE and water with a small amount of sodium thiosulfate. The organic layer was washed with water and concentrated to an oil. The oil was charged slowly into a mixture of water (2 L) and DMF (300 ml) with a small amount of seed at 5° C. The crystals were filtered and dried to give 3 (400 g, 93% yield).

Workup

  1. customwent up to 29° C. from 17° C
  2. filtrationThe mixture was filtrated
  3. washwashed with MTBE
  4. concentrationconcentrated
  5. additionThe residue was treated with MTBE and water with a small amount of sodium thiosulfate
  6. washThe organic layer was washed with water
  7. concentrationconcentrated to an oil
  8. additionThe oil was charged slowly into a mixture of water (2 L) and DMF (300 ml) with a small amount of seed at 5° C
  9. filtrationThe crystals were filtered
  10. customdried

Sources & evidence

ORD record
ord-339ba276d98a4adb9bac5f91a204060a
Source dataset
uspto-grants-2015_11
Patent number
US09174989B2

Reaction notes

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