Benzyl chloroformate → HCID 68948944, compound

HRID 2116728Notes

Reaction equation

HRID 2116728 reaction equation
[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[C:12](NC)[NH:13]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C[CH2:21][N:22](C(C)C)C(C)C.[CH:29]1[CH:34]=[CH:33][C:32]([CH2:35][O:36][C:37](Cl)=[O:38])=[CH:31][CH:30]=1>C(Cl)Cl>[CH2:35]([O:36][C:37](=[O:38])[NH:22][CH2:21][C:12]1[NH:13][C:14]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:18])[CH3:19])[CH:15]=2)[C:32]1[CH:33]=[CH:34][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 68949138HCID 68949138, compound

Product 1

HCID 68948944HCID 68948944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[6-(tert-Butyl-dimethyl-silanyloxy)-1H-indol-2-yl]-methylamine (0.70 g, 1.01 mmol) is dissolved in DCM (10 ml), cooled to 0° C. DIEA (0.35 ml, 2.02 mmol) and Cbz-Cl (0.17 g, 1.01 mmol) are added. The mixture is stirred for 1 hour at room temperature. The reaction mixture is concentrated and the residue is purified by column chromatography (10% ethyl acetate in hexanes) to provide [6-(tert-Butyl-dimethyl-silanyloxy)-1H-indol-2-ylmethyl]-carbamic acid benzyl ester.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is purified by column chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1ce532aa8e1a459cbcbeac12be93cae9
Source dataset
uspto-grants-2008_10
Patent number
US07439249B2

Reaction notes

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