Imidazole → (2s)-2-Tert-butoxycarbonylamino-3-[5-(tert-butyl-dimethyl-silanyloxy)-1h-indol-3-yl]-propionic acid methyl ester

HRID 2307823Notes

Reaction equation

HRID 2307823 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[NH:8][CH:7]=1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].N1C=CN=C1.CCOC(C)=O>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:24])[C@@H:4]([NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH:13]=2)[NH:8][CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 23378123HCID 23378123, compound

Product 1

HCID 69918141(2s)-2-Tert-butoxycarbonylamino-3-[5-(tert-butyl-dimethyl-silanyloxy)-1h-indol-3-yl]-propionic acid methyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 400A (1.20 g, 3.59 mmol) in DMF (20 mL) was added t-butyldimethylsilyl chloride (649 mg, 4.3 mmol), imidazole (293 mg, 4.3 mmol) and DMAP (50 mg) at rt. The reaction mixture was stirred at rt for 16 hours. EtOAc (100 mL) was added and the mixture was washed with brine (100 mL) and water (100 mL). The organic phase was concentrated and the residual oil was purified by flash chromatography (10-40% EtOAc in hexane) to give the desire product (1.6 g, 100%). MS (DCI) m/z 466 (M+18)+.

Workup

  1. washthe mixture was washed with brine (100 mL) and water (100 mL)
  2. concentrationThe organic phase was concentrated
  3. customthe residual oil was purified by flash chromatography (10-40% EtOAc in hexane)

Sources & evidence

ORD record
ord-2a94b29cae664de7bcacbb19ec519169
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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