Acetic Acid → 7-Fluorotryptophan

HRID 1725829

반응식

HRID 1725829 반응식
C([O:3][C:4](=[O:25])[C:5]([CH2:14][C:15]1[C:23]2[C:18](=[C:19]([F:24])[CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)([NH:11]C=O)C(OCC)=O)C.[OH-].[Na+].C(O)(=O)C>C1COCC1>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:18]=1[NH:17][CH:16]=[C:15]2[CH2:14][C@@H:5]([C:4]([OH:25])=[O:3])[NH2:11]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 575633012-(7-Fluoro-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester

생성물 1

HCID 159301487-Fluorotryptophan수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-(7-Fluoro-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester in THF was treated with NaOH (300 mg in 10 mL water) at room temperature for 24 hr. The mixture was slowly acidified with acetic acid (5 mL) and then refluxed for 24 hr. The reaction mixture was concentrated under vacuum, and treated with dil. HCl (10 mL, 3M) and then again refluxed for ˜16 h. The reaction was allowed to cool to room temperature. The pH was adjusted to 6.0 with 2M KOH. The white solid that formed was filtered, washed with water, and dried under vacuum to give 7-fluoro-tryptophan (282 mg, 52%): mp 256-261° C., 1H NMR (500 MHz, DMSO-d6): 2.92-2.97 (dd, J=8.5 and 15 Hz, 1H), 3.25-3.29 (dd, J=4.0 and 15 Hz, 1H), 3.38-3.41 (dd, J=4.0 and 8.5 Hz, 1H), 6.87-6.96 (m, 2H), 7.25 (s, 1H), 7.37 (d, J=7.5 Hz, 1H), 11.36 (s, 1H).

후처리

  1. temperaturerefluxed for 24 hr
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additiontreated with dil. HCl (10 mL, 3M)
  4. temperatureagain refluxed for ˜16 h
  5. customThe white solid that formed
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-e8f4fb08bb854c3ba511130029c52cf3
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491743B2

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