Triethylamine → HCID 14182516, 화합물

HRID 1252627

반응식

HRID 1252627 반응식
C(N(CC)CC)C.[OH:8][C:9]1[C:10](=[O:26])[CH:11]=[C:12]([CH2:22][C:23]([OH:25])=O)[N:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=1.ON1C2C=CC=CC=2N=N1.CN(C)N1C=CC=CC1.[NH2:46][N:47]1[CH2:51][CH2:50][NH:49][C:48]1=[O:52].C1(N=C=NC2CCCCC2)CCCCC1.CN([Si](C)(C)C)C(=O)C(F)(F)F>CN(C)C=O.C(#N)C.ClCCl>[OH:8][C:9]1[C:10](=[O:26])[CH:11]=[C:12]([CH2:22][C:23]([NH:46][N:47]2[CH2:51][CH2:50][NH:49][C:48]2=[O:52])=[O:25])[N:13]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:14]=1

참가 물질

11

반응물 7

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 757711-HydroxybenzotriazoleHCID 1816971-Aminoimidazolidin-2-oneHCID 6453552N,N-dimethylpyridin-1-amineHCID 141825151,4-Dihydro-5-hydroxy-4-oxo-1-(phenylmethyl)-2-pyridineacetic acid

생성물 1

HCID 14182516HCID 14182516, 화합물

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

4.99 ml (35.83 mmol) of triethylamine was added to a suspension of 9.29 g (35.83 mmol) of 1,4-dihydro-5-hydroxy-4-oxo-1-(phenylmethyl)-2-pyridineacetic acid, 0.28 g (1.79 mmol) of N-hydroxybenzotriazole, 0.22 g (1.79 mmol) of N-dimethylaminopyridine, 3.62 g (35.83 mmol) of N-aminoimidazolidinone and 8.13 g (39.41 mmol) of dicyclohexylcarbodiimide in 115 ml of dry dimethylformamide. Stirring was continued overnight at room temperature. The precipitated dicyclohexylurea was filtered off, washed with dimethylformamide, and the filtrate was evaporated in vacuo to leave a residue, which became crystalline by stirring with 110 ml of dichloromethane. The precipitate was collected by suction and dried in vacuo. To a suspension of this crude material in 65 ml of dry acetonitrile, 14.0 ml (71.6 mmol) of N-methyl-N-trimethylsilyltrifluoroacetamide was added. After having been stirred for 30 minutes at room temperature, the undissolved dicyclohexylurea was filtered off and the filtrate was evaporated in vacuo. The oily residue was boiled in 70 ml of methanol for 15 minutes and cooled. The precipitate was collected by suction, washed successively with methanol, methanol/ether (1:1) and ether and dried in vacuo. Yield: 8.7 g; sint. 242° C., melting point 260°-265° C. dec.

후처리

  1. filtrationThe precipitated dicyclohexylurea was filtered off
  2. washwashed with dimethylformamide
  3. customthe filtrate was evaporated in vacuo
  4. customto leave a residue, which
  5. customThe precipitate was collected by suction
  6. customdried in vacuo
  7. additionwas added
  8. stirringAfter having been stirred for 30 minutes at room temperature
  9. filtrationthe undissolved dicyclohexylurea was filtered off
  10. customthe filtrate was evaporated in vacuo
  11. waitThe oily residue was boiled in 70 ml of methanol for 15 minutes
  12. temperaturecooled
  13. customThe precipitate was collected by suction
  14. washwashed successively with methanol, methanol/ether (1:1) and ether
  15. customdried in vacuo
  16. custom242° C., melting point 260°-265° C. dec.

출처 및 근거

ORD 기록
ord-6c5430be47b244f0aaacf30c6f51cdea
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04743685

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