Bicarbonate Ion → Tert-butyl(3-(3-methylthioureido)propyl)carbamate

HRID 708490Notes

Reaction equation

HRID 708490 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([NH2:14])=[S:13])([CH3:4])([CH3:3])[CH3:2].IC.[C:18](=O)(O)[O-]>CO>[NH:14]=[C:12]([NH:11][CH2:10][CH2:9][CH2:8][NH:7][C:6](=[O:15])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[S:13][CH3:18].[CH3:18][NH:14][C:12](=[S:13])[NH:11][CH2:10][CH2:9][CH2:8][NH:7][C:6](=[O:15])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 6328Methyl iodideHCID 20616909tert-Butyl 3-thioureidopropylcarbamate

Product 2

HCID 131733811Tert-butyl(3-(3-methylthioureido)propyl)carbamateYield 87%HCID 178504038HCID 178504038, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl(3-thioureidopropyl)carbamate (0.29 g, 1.28 mmol) in MeOH (8 mL) was added iodomethane (80 μL, 1.29 mmol). After stirring at rt for 18 h, bicarbonate on polymer support (0.5 g, 3.5 mmol NaCO3/g resin) was added to the reaction mixture. After 30 min, the reaction mixture was filtered, and the filtrate was concentrated in vacuo to give the desired product along with the N-methylated product, tert-butyl (3-(3-methylthioureido)propyl)carbamate (0.28 g, 87%, 2:1 ratio). The crude residue was used as such in the following step. LCMS: Rt=0.44 min and 0.49 min, m/z=248.1 (M+1) Method 2m_acidic.

Workup

  1. waitAfter 30 min
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-af29b7021fbf4397af950f2ff22e4026
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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