Ammonia → tert-Butyl 2-thioureidoacetate

HRID 1755434Notes

Reaction equation

HRID 1755434 reaction equation
[NH2:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:10](N1C=CC=CC1=O)([N:12]1C=CC=CC1=O)=[S:11].N.CO>C(Cl)Cl>[NH:1]([CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:10]([NH2:12])=[S:11]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 151417Glycine tert-butyl esterHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridone

Product 1

HCID 57225720tert-Butyl 2-thioureidoacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred suspension of tert-butyl 2-aminoacetate (11.2 g, 85 mmol) in CH2Cl2 (200 mL) under nitrogen is added 1,1′-thiocarbonyldipyridin-2(1H)-one (21 g, 90 mmol) and the resulting mixture is stirred at room temp. for 18 h. The solvent is removed in vacuo, the residue treated with 2M ammonia in methanol (600 mL, 1200 mmol) and stirred at room temperature for 45 min. The solvent is removed in vacuo and dried under high vacuum to give the title compound as a reddish oil that is used “as is” without further purification in the next step. LC/MS (Condition A): ret. T=2.19 min, (M+H)+ 191—actually see (M−55) 134.95 (this is characteristic of BOC fragmentation pattern).

Workup

  1. customThe solvent is removed in vacuo
  2. stirringstirred at room temperature for 45 min
  3. customThe solvent is removed in vacuo
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-3a4a769d4f4a40a2b6a52cf533babe2d
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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