PyBOP → N-Boc-4-iodo-L-phenylalanine ethyl ester

HRID 556392Notes

Reaction equation

HRID 556392 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)C[CH2:22]1.F[P-](F)(F)(F)(F)F>CCO.CN(C1C=CN=CC=1)C>[CH2:21]([O:11][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)[CH3:22]

Participants

5

Reactant 2

HCID 2724699PyBOPHCID 2755956(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid

Product 1

HCID 66909227N-Boc-4-iodo-L-phenylalanine ethyl esterYield 93.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)-2-tert-butoxycarbonylamino-3-(4-iodo-phenyl)-propionic acid (3 g) in anh. EtOH (38 mL) was added DMAP (187 mg) and PyBOP (6 g). The reaction mixture was stirred on at RT and partitioned between EA and water. The org. phase was separated, washed with 10% aq. citric acid and sat. aq. NaHCO3, dried (Na2SO4) and evaporated off. The resulting crude material was purified by CC (Hept/EA 1/0 to 0/1) to afford the title compound as a white solid (3 g).

Workup

  1. custompartitioned between EA and water
  2. customphase was separated
  3. washwashed with 10% aq. citric acid and sat. aq. NaHCO3
  4. dry with materialdried (Na2SO4)
  5. customevaporated off
  6. customThe resulting crude material was purified by CC (Hept/EA 1/0 to 0/1)

Sources & evidence

ORD record
ord-1273e2f94a5c4e9180889ab29544f177
Source dataset
uspto-grants-2011_11
Patent number
US08058263B2

Reaction notes

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