Iodine → HCID 57950670, 화합물

HRID 598864노트

반응식

HRID 598864 반응식
Cl.[NH2:2][C@@H:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[CH2:4][C:5](O)=[O:6].[BH4-].[Na+].II>C1COCC1>[NH2:2][C@@H:3]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=1)[CH2:4][CH2:5][OH:6]

참가 물질

5

반응물 3

HCID 807IodineHCID 2761665(3S)-3-Amino-4-[4-(trifluoromethyl)phenyl]butanoic acid--hydrogen chloride (1/1)HCID 4311764Sodium borohydride

생성물 1

HCID 57950670HCID 57950670, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

(S)-3-Amino-4-(4-(trifluoromethyl)phenyl)butanoic acid hydrochloride (950 mg, 3.84 mmol) and NaBH4 (362 mg, 9.6 mmol) were dissolved in 20 mL THF and cooled to 0° C. A solution of I2 (974 mg, 3.84 mmol) in 5 mL THF was added at 0° C. over a period of 20 minutes. The cooling bath was removed and the reaction was heated at reflux over night. The reaction was cooled to room temperature and carefully hydrolyzed with MeOH until gas evolution ceased. The clear solution was evaporated in vacuo, 20 mL KOH (20%, aqueous) was added, and the reaction was stirred for 3 hours. The reaction was extracted with DCM (3×100 mL), dried over MgSO4 and evaporated. The title compound was obtained as a white solid and used without further purification in the next reaction. LCMS (API-ES) m/z (%): 234.0 (100%, M++H).

후처리

  1. customThe cooling bath was removed
  2. temperaturethe reaction was heated
  3. temperatureat reflux over night
  4. temperatureThe reaction was cooled to room temperature
  5. customThe clear solution was evaporated in vacuo, 20 mL KOH (20%, aqueous)
  6. additionwas added
  7. extractionThe reaction was extracted with DCM (3×100 mL)
  8. dry with materialdried over MgSO4
  9. customevaporated

출처 및 근거

ORD 기록
ord-a6d6b1c12688497bbd3b57496d917630
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897619B2

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