Formaldehyde → N-Methylleucine

HRID 1089821

반응식

HRID 1089821 반응식
C1C2C(CO[C:16]([NH:18][C@H:19]([C:24]([OH:26])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=O)C3C(=CC=CC=3)C=2C=CC=1.C=O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:16][NH:18][C@H:19]([C:24]([OH:26])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22]

참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 1549133Fmoc-leucine

생성물 1

HCID 2777993N-Methylleucine수율 117.1%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

실험 절차

A suspension of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine (1.67 g, 5 mmol) in toluene(100 ml) was charged with paraformaldehyde (1 g, 33.3 mmol) and 4-toluenesulfonic acid (100 mg, catalytic). The mixture was refluxed for 30 minutes in a Dean Stark apparatus for azeotropic distillation. The solution was washed with a saturated solution of sodium bicarbonate (×2), dried over magnesium sulfate and evaporated. The resulting oil in a 1:1 mixture of chloroform:trifluoroacetic acid (50 ml), at room temperature, was charged with triethylsilane (2.38 ml, 15 mmol). Stirring was continued for 22 hr. The solvents were removed in vacuum and the oil was crystallized from a mixture of ether:hexane. Recrystalyzation from EtOAc:hexane afforded 0.85 g (46%) of the product as a colorless solid, mp 101°-3° C.

후처리

  1. temperatureThe mixture was refluxed for 30 minutes in a Dean Stark apparatus for azeotropic distillation
  2. washThe solution was washed with a saturated solution of sodium bicarbonate (×2)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. additionThe resulting oil in a 1:1 mixture of chloroform
  6. customThe solvents were removed in vacuum
  7. customthe oil was crystallized from a mixture of ether

출처 및 근거

ORD 기록
ord-53ad8a2361374f15a4ed27622a2ceb26
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05079260

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