Chlorotrimethylsilane → (2S)-2-acetamido-3-(4-iodophenyl)propanoic acid

HRID 2183534

反応式

HRID 2183534 の反応式
[I:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][CH:7]([C:9]([OH:11])=[O:10])[NH2:8])=[CH:4][CH:3]=1.[Si](Cl)(C)(C)C.C(N(CC)CC)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>ClCCl>[C:26]([NH:8][C@H:7]([C:9]([OH:11])=[O:10])[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:13][CH:12]=1)(=[O:28])[CH3:27]

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 51523122-Amino-3-(4-iodophenyl)propionic acid

生成物 1

HCID 68624886(2S)-2-acetamido-3-(4-iodophenyl)propanoic acid収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of 15 g (51 mmol) of 4-iodo-D,L-phenylalanine and 16.2 ml (127.5 mmol) of Me3SiCl in 150 mL of dichloromethane was heated at reflux for 1 h under N2. The reaction mixture was cooled to 0° C. with an ice bath and 17.7 mL (127 mmol) of triethyl amine was added, followed by 5.83 mL (61.2 mmol) of acetic anhydride. The mixture was stirred at 0° C. for 30 min, then warmed up to room temperature and stirred for another 30 min. The reaction was quenched by adding 1M aqueous sodium hydroxide and then the mixture was acidified with 2M aqueous hydrogen chloride to pH 1. The precipitate was collected by filtration and dried under vacuum to afford 16 g (95%) of N-acetyl-4-iodophenylalanine as a white solid: 1H NMR (DMSO-d6) 8.19 (d, 1H), 7.61 (d, 2H), 7.02 (d, 2H), 4.39-4.31 (m, 1H), 3.01-2.92 (dd, 1H), 3.80-2.69 (dd, 1H), 2.67 (s, 3H).

後処理

  1. temperatureat reflux for 1 h under N2
  2. temperaturewarmed up to room temperature
  3. stirringstirred for another 30 min
  4. customThe reaction was quenched
  5. additionby adding 1M aqueous sodium hydroxide
  6. filtrationThe precipitate was collected by filtration
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-3053ea7609154a6385d5e8cb13e41d4a
出典データセット
uspto-grants-2005_05
特許番号
US06900213B2

関連ノート

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