Tetrahydrofuran → HCID 178425720, 화합물

HRID 1629761노트

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HRID 1629761 반응식
[NH2:1][C@@:2]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[CH:19][CH:18]=1)([C:13]([F:16])([F:15])[F:14])[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=[O:5].C1CCC(N=C=NC2CCCCC2)CC1.[N:46]1[N:47](CC(O)=O)[N:48]=[N:49][CH:50]=1.C1C[O:58][CH2:57][CH2:56]1>>[NH:46]1[C:50]([CH2:56][C:57]([NH:1][C:2]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][C:27]([F:28])([F:29])[F:30])=[CH:19][CH:18]=2)([CH2:3][C:4](=[O:5])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[C:13]([F:16])([F:15])[F:14])=[O:58])=[N:49][N:48]=[N:47]1

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 10868DicyclohexylcarbodiimideHCID 890302H-Tetrazol-2-acetic acidHCID 86685849(S)-3-Amino-4,4,4-trifluoro-1-p-tolyl-3-(4-(4,4,4-trifluorobutoxy)phenyl)-butan-1-one

생성물 1

HCID 178425720HCID 178425720, 화합물수율 152%

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온도
0 °C

실험 절차

To a solution of Intermediate 2F (789 mg, 1.82 mmol) in anhydrous THF (9 ml) at 0° C. was added DCC (1.13 g, 5.46 mmol). 2-Tetrazole acetic acid (700 mg, 5.46 mmol) was added dropwise as a suspension in anhydrous THF (8 mL). The reaction was stirred at 0° C. for 1 h and then at rt overnight. The reaction was filtered and solids were rinsed with THF. The filtrate was diluted with EtOAc (40 mL), washed with sat'd Na2CO3 and sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated to provide Intermediate 2G (1.5 g, 152%) as a reddish brown solid. Intermediate 2G. was used in the next step without further purification. LCMS Anal. Calc'd for C24H23F6N5O3 543.46, found [M+H] 543.9.

후처리

  1. customat rt
  2. customovernight
  3. filtrationThe reaction was filtered
  4. washsolids were rinsed with THF
  5. additionThe filtrate was diluted with EtOAc (40 mL)
  6. washwashed with sat'd Na2CO3
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ee86fc6a067d4bb5af4ffcb248898c30
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791091B2

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