Trimethylsilyl iodide → 2-Amino-3-(6-benzyloxy-pyridin-3-yl)-propionic acid methyl ester

HRID 2250226Notes

Reaction equation

HRID 2250226 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH:4]([NH:20]C(OCC1C=CC=CC=1)=O)[CH2:5][C:6]1[CH:7]=[N:8][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:11]=1.C[Si](I)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:31])[CH:4]([NH2:20])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 588644962-Benzyloxycarbonylamino-3-(6-benzyloxy-pyridin-3-yl)-propionic acid methyl ester

Product 1

HCID 588642862-Amino-3-(6-benzyloxy-pyridin-3-yl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-benzyloxycarbonylamino-3-(6-benzyloxy-pyridin-3-yl)-propionic acid methyl ester (130 mg, 0.31 mmol) in methylene chloride (5 mL, 0° C.) was added trimethylsilyl iodide (44 μL, 1.0 equiv). The ice bath was removed and stirring continued for 1 h. Reaction was poured into saturated sodium bicarbonate, extracted with ethyl acetate (3×), washed with brine, dried over magnesium sulfate, and concentrated to give 81 mg (91%) which was used without purification. Mass spec.: 287.37 (MH)+.

Workup

  1. customThe ice bath was removed
  2. customReaction
  3. extractionextracted with ethyl acetate (3×)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give 81 mg (91%) which
  8. customwas used without purification

Sources & evidence

ORD record
ord-304e1559f05742868628da6829e1eeaa
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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