Trifluoroacetic acid → (S)-2-Amino-3-(4-iodophenyl)propanamide

HRID 216902Notes

Reaction equation

HRID 216902 reaction equation
[NH2:1][C:2](=[O:20])[C@@H:3]([NH:12]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:12][C@@H:3]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([I:11])=[CH:9][CH:10]=1)[C:2]([NH2:1])=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57999635(S)-tert-Butyl (1-amino-3-(4-iodophenyl)-1-oxopropan-2-yl)carbamate

Product 1

HCID 447705(S)-2-Amino-3-(4-iodophenyl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamate (Example 1, step (i), 2.41 g) was stirred in dichloromethane (125 mL) and to the suspension was added trifluoroacetic acid (8 mL). The mixture was stirred for 2 h and then concentrated to ˜12 mL in vacuo. The residue was stirred for 2 days, dissolved in ethyl acetate/dichloromethane and washed with water containing an excess of sodium bicarbonate. The organic layer was dried and evaporated to the sub-titled compound (1.52 g).

Workup

  1. concentrationconcentrated to ˜12 mL in vacuo
  2. stirringThe residue was stirred for 2 days
  3. dissolutiondissolved in ethyl acetate/dichloromethane
  4. washwashed with water containing an excess of sodium bicarbonate
  5. customThe organic layer was dried
  6. customevaporated to the sub-titled compound (1.52 g)

Sources & evidence

ORD record
ord-d85c8daa8e99494ea7e46176865567d7
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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