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

HRID 1439703노트

반응식

HRID 1439703 반응식
[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]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 2724879(2S,3S)-3-methylpyrrolidine-2-carboxylic AcidHCID 86585469HCID 86585469, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-5b069f5b73304035ac72262a2c554839
출처 데이터셋
uspto-grants-1977_11
특허 번호
US04060603

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