Triethylamine → N-Bromoacetyl-S-triphenylmethyl-L-cysteine ethyl ester

HRID 1417916ノート

反応式

HRID 1417916 の反応式
[CH2:1]([O:3][C:4](=[O:28])[C@H:5]([CH2:7][S:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:6])[CH3:2].C(N(CC)CC)C.[Br:36][CH2:37][C:38](Br)=[O:39]>C1COCC1>[CH2:1]([O:3][C:4](=[O:28])[C@H:5]([CH2:7][S:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH:6][C:38](=[O:39])[CH2:37][Br:36])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 21144450S-trityl-cysteine ethyl ester

生成物 1

HCID 57318726N-Bromoacetyl-S-triphenylmethyl-L-cysteine ethyl ester収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of S-triphenylmethyl-L-cysteine ethyl ester (18 g, 46 mmol.) and triethylamine (6.4 mL, 46 mmol.) in dry THF (250 mL) under nitrogen was cooled to 0° C. A solution of bromoacetyl bromide (9.28 g, 46 mmol.) in dry THF (60 mL) was added dropwise during which time the solution turned cloudy. The reaction mixture was stirred at 0° C. for 1 h and then at room temperature for 1 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give an oil. The oil was partitioned between methylene chloride and water (60 mL each), the organic layer washed with 5% HCl, NaHCO3, dried (magnesium sulfate), filtered, and the volatiles removed to give the desired product (69%).

後処理

  1. waitat room temperature for 1 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give an oil
  5. customThe oil was partitioned between methylene chloride and water (60 mL each)
  6. washthe organic layer washed with 5% HCl, NaHCO3
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. customthe volatiles removed

出典と根拠

ORDレコード
ord-1fc35abb2fa544139782d5f5e679e27f
出典データセット
uspto-grants-1999_03
特許番号
US05879657

反応ノート

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