Chloroacetone → HCID 68918267, compound

HRID 1808143Notes

Reaction equation

HRID 1808143 reaction equation
[C:1](=[O:22])([O:3][C@H:4]([CH:8]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[C:5]([NH2:7])=[S:6])[NH2:2].C(=O)([O-])O.[K+].Cl[CH2:29][C:30](=[O:32])[CH3:31]>C(COC)OC>[C:1](=[O:22])([O:3][C@@H:4]([C:5]1[S:6][CH2:29][C:30]([OH:32])([CH3:31])[N:7]=1)[CH:8]([C:18]([CH3:19])([CH3:21])[CH3:20])[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[NH2:2]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 516893Potassium BicarbonateHCID 86634824HCID 86634824, compound

Product 1

HCID 68918267HCID 68918267, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
45 °C

Procedure

A solution of (R)-tert-butyl-1-amino-3-(1H-Indol-3-yl)-1-thioxopropan-2-yl carbamate (6.49 g, 20.3 mmol) in anhydrous dimethoxyethane (100 mL) was mixed with powdered potassium hydrogencarbonate (10.1 g, 101 mmol) and chloroacetone (9.69 g, 8.4 mL, 101 mmol) and stirred for 8 h at 70° C. and over the weekend at 45° C. The reaction mixture was then filtered and the filtrate concentrated to low volume in a vacuum.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate concentrated to low volume in a vacuum

Sources & evidence

ORD record
ord-193828385e6043a9b23d07284fc59ee7
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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