Sodium Hydroxide → tert-Butyl 3-thioureidopropylcarbamate

HRID 1755461Notes

Reaction equation

HRID 1755461 reaction equation
C([NH:9][C:10](=[S:23])[NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=O)C1C=CC=CC=1.[OH-].[Na+]>CO>[NH:11]([CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[C:10]([NH2:9])=[S:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14280415tert-Butyl 3-(3-benzoylthioureido)propylcarbamate

Product 1

HCID 20616909tert-Butyl 3-thioureidopropylcarbamateYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of material from Example 58 (6.89 g, 20.43 mmol) in MeOH (40 mL) is slowly added aqueous 5M NaOH (4.49 mL, 22.47 mmol) and the reaction is allowed to stir for 1 h at room temp. The solvent is removed in vacuo, the residue is neutralized with acetic acid and partitioned between water and EtOAc. The water layer is extracted with EtOAC, the organic layers are combined, washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give 3.43 g (50.2%) of the title compound. LC/MS (Condition A): ret. T=2.54 min, (M+Na) 256.13.

Workup

  1. customThe solvent is removed in vacuo
  2. custompartitioned between water and EtOAc
  3. extractionThe water layer is extracted with EtOAC
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-afabd929efe7455c8ee92fb226c440aa
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

Loading…