Hydrochloric Acid → 2-Iodo-L-Phenylalanine,hydrochloride

HRID 369780Notes

Reaction equation

HRID 369780 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.[ClH:32].C(C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[ClH:32].[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 207060262-Iodo-L-Phenylalanine,hydrochlorideYield 94%

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 6 N 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-c2bd513616f1450e8133e8a4478a1863
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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