Triethylamine → N-(5-Fluoro-2-nitrophenyl)-S-methyl-L-cysteine

HRID 876

反応式

HRID 876 の反応式
[CH3:1][S:2][CH2:3][C@@H:4]([C:6]([OH:8])=[O:7])[NH2:5].C(N(CC)CC)C.F[C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]>O.CC(C)=O>[F:23][C:21]1[CH:20]=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[C:17]([NH:5][C@H:4]([C:6]([OH:8])=[O:7])[CH2:3][S:2][CH3:1])[CH:22]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 24417(-)-S-Methyl-L-cysteineHCID 679672,4-Difluoronitrobenzene

生成物 1

HCID 57293179N-(5-Fluoro-2-nitrophenyl)-S-methyl-L-cysteine

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

16.2 g of (-)-S-Methyl-L-cysteine (0.1 mol) are suspended in a mixture of 120 ml of water and 120 ml of acetone in a four-necked flask under N2. 30.4 ml (22.2 g) of triethylamine (0.22 mol) are added rapidly while stirring. 15.9 g of 2,4-difluoronitrobenzene (0.1 mol) are added, with further stirring, to the resulting yellow solution. The mixture is heated to reflux for 7.5 hours while stirring (orange-colored solution) and the acetone is then stripped off under reduced pressure on a rotary evaporator; the aqueous residue is transferred to a separating funnel and extracted 2× with approximately 50 ml of methyl tert-butyl ether (MTB ether). This extract is composed, in the main, of 2,4-difluoronitrobenzene and is discarded. The aqueous phase is transferred to a four-necked flask and 150 ml of MTB ether are added to it, after which the mixture is adjusted, while being cooled (<25° C.), to pH 1 with approximately 25 ml of 38% sulfuric acid. The mixture is then stirred thoroughly until clear phases are formed. The ether phase is separated off and the aqueous phase is extracted once again with 50 ml of MTB ether. The extracts are dried over sodium sulfate and evaporated on a rotary evaporator. The yield comprises 27 g of a yellow oil which soon solidifies. M.p. 147° (from water/methanol).

後処理

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 7.5 hours
  3. stirringwhile stirring (orange-colored solution)
  4. customthe acetone is then stripped off under reduced pressure on a rotary evaporator
  5. customthe aqueous residue is transferred to a separating funnel
  6. extractionextracted 2× with approximately 50 ml of methyl tert-butyl ether (MTB ether)
  7. customThe aqueous phase is transferred to a four-necked flask
  8. addition150 ml of MTB ether are added to it
  9. temperaturewhile being cooled (<25° C.)
  10. stirringThe mixture is then stirred thoroughly until clear phases
  11. customare formed
  12. customThe ether phase is separated off
  13. extractionthe aqueous phase is extracted once again with 50 ml of MTB ether
  14. dry with materialThe extracts are dried over sodium sulfate
  15. customevaporated on a rotary evaporator

出典と根拠

ORDレコード
ord-f2917c57d8924daa80ca9144336b9913
出典データセット
uspto-grants-1998_03
特許番号
US05723461

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