Hydrochloric Acid → 2-Iodo-L-Phenylalanine

HRID 429890Notes

Reaction equation

HRID 429890 reaction equation
C([O:5][C:6](=[O:17])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[I:16])[NH2:8])(C)(C)C.C(=N)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.C(C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[I:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][C@@H:7]([C:6]([OH:17])=[O:5])[NH2:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3102BenzophenoneHCID 86755969HCID 86755969, compound

Product 1

HCID 207060272-Iodo-L-PhenylalanineYield 109.7%

Procedure

A 500 mL round bottomed flask equipped with a reflux condenser and a magnetic stirrer was charged with 15.72 g of 2-iodo-L-phenylalanine tert-butyl ester-benzophenone imine (86% ee) and 165 mL of 6N aqueous HCl. The mixture was heated at reflux with stirring for 4 h and cooled to RT to afford a mixture of white crystalline solid and an immicible organic phase (benzophenone). The mixture was partitioned between water (100 mL) and ethyl ether (70 mL). The aqueous phase was separated, washed with four additional 70 mL portions of ether and concentrated in vacuo to dryness to give 9.5 g (94%) of 2-iodo-L-phenylalanine.HCl as a fluffy white solid, m.p. 240° C. (dec).

Workup

  1. customA 500 mL round bottomed flask equipped with a reflux condenser and a magnetic stirrer
  2. temperatureThe mixture was heated
  3. temperatureat reflux
  4. customto afford
  5. additiona mixture of white crystalline solid
  6. customThe mixture was partitioned between water (100 mL) and ethyl ether (70 mL)
  7. customThe aqueous phase was separated
  8. washwashed with four additional 70 mL portions of ether
  9. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-17ff2e72e66a4ebf81b00ff94dfbaee8
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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