Ammonia → tert-Butyl 2-thioureidoacetate

HRID 1755434ノート

反応式

HRID 1755434 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 57225720tert-Butyl 2-thioureidoacetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3a4a769d4f4a40a2b6a52cf533babe2d
出典データセット
uspto-grants-2015_10
特許番号
US09169295B2

反応ノート

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