Potassium bisulfate → benzyl N-[3-(2-aminoethyl)pyrrolidine-1-carboximidoyl]carbamate

HRID 1450713

反応式

HRID 1450713 の反応式
C(OC([NH:8][CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)=O)(C)(C)C.[CH2:16]([O:23][C:24]([NH:26][C:27](=[NH:30])SC)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1>[CH2:16]([O:23][C:24]([NH:26][C:27]([N:13]1[CH2:14][CH2:15][CH:11]([CH2:10][CH2:9][NH2:8])[CH2:12]1)=[NH:30])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 516920Potassium bisulfateHCID 21955469tert-butyl N-[2-(pyrrolidin-3-yl)ethyl]carbamateHCID 140362141Benzyl [amino(methylsulfanyl)methylene]carbamate

生成物 1

HCID 140379083benzyl N-[3-(2-aminoethyl)pyrrolidine-1-carboximidoyl]carbamate収率 67,529.203%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

2.18 g (0.0102 mmole) (3RS)-3-(N-tertbutyloxycarbonylaminoethyl) pyrrolidine and 2.81 g (0.0125 mole) N-benzyloxycarbonyl-S-methylisothiourea was dissolved in 30 ml toluene and heated to 60°-70° C. for eight hours followed by stirring at room temperature for one day. 0.3M KHSO4 -solution was added and the water layer was washed with a mixture of the toluene and ethyl acetate and left for 2 days under which time the Boc group was removed. The acidic water phase was made alkaline and extracted four times with CH2Cl2. The combined organic layer was dried (Na2SO4), filtered and evaporated to yield 2.0 g (51%) of the title compound.

後処理

  1. temperatureheated to 60°-70° C. for eight hours
  2. washthe water layer was washed with a mixture of the toluene and ethyl acetate
  3. waitleft for 2 days under which time the Boc group
  4. customwas removed
  5. extractionextracted four times with CH2Cl2
  6. dry with materialThe combined organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-11d7b575dc2a42e694559ae489af15f3
出典データセット
uspto-grants-1997_02
特許番号
US05602253

関連ノート

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