Formaldehyde → N-Methylleucine

HRID 1089821

反応式

HRID 1089821 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 2777993N-Methylleucine収率 117.1%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-53ad8a2361374f15a4ed27622a2ceb26
出典データセット
uspto-grants-1992_01
特許番号
US05079260

関連ノート

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