Triethylamine → rac-(3S)-1-(tert-butoxycarbonyl)-3-methyl-L-proline

HRID 1439703ノート

反応式

HRID 1439703 の反応式
[CH2:1](N(CC)CC)C.[C:8](=[O:24])([O-])[O:9][C:10]1[CH:15]=C(Cl)C(Cl)=C(C(C)(C)C)[C:11]=1Cl.[CH3:25][C@H:26]1[CH2:30][CH2:29][NH:28][C@@H:27]1[C:31]([OH:33])=[O:32]>C(O)(C)(C)C.O>[C:10]([O:9][C:8]([N:28]1[CH2:29][CH2:30][C@H:26]([CH3:25])[C@H:27]1[C:31]([OH:33])=[O:32])=[O:24])([CH3:11])([CH3:15])[CH3:1]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 2724879(2S,3S)-3-methylpyrrolidine-2-carboxylic AcidHCID 86585469HCID 86585469、化合物

生成物 1

HCID 22800293rac-(3S)-1-(tert-butoxycarbonyl)-3-methyl-L-proline

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

Triethylamine (3.5 ml) and t-butyl-2,4,5-trichlorophenyl carbonate (3.5 g) were added to a solution of trans-3-methyl-L-proline (1.25 g) in t-butanol (12 ml) and water (8 ml). The mixture was heated to 60° for 2 hours, evaporated, the residue dissolved in 1 N sodium bicarbonate solution (50 ml) and the solution washed with ether. Excess solid citric acid was added, the product extracted into ethyl acetate, the combined extracts dried (Na2SO4) and evaporated giving a crude crystalline product (1.6 g). Recrystallisation from ethyl acetate/light petroleum (40°-60°) gave the desired product (1.33 g), m.p. 146°-150° [α]D20 - 60.1° (c, 1.0, chloroform)

後処理

  1. temperatureThe mixture was heated to 60° for 2 hours
  2. customevaporated
  3. dissolutionthe residue dissolved in 1 N sodium bicarbonate solution (50 ml)
  4. washthe solution washed with ether
  5. additionExcess solid citric acid was added
  6. extractionthe product extracted into ethyl acetate
  7. dry with materialthe combined extracts dried (Na2SO4)
  8. customevaporated

出典と根拠

ORDレコード
ord-5b069f5b73304035ac72262a2c554839
出典データセット
uspto-grants-1977_11
特許番号
US04060603

反応ノート

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