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

HRID 2183532

반응식

HRID 2183532 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e1426e67f5c2421a9645546d0ccdc35e
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900213B2

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