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Dicyclohexylcarbodiimide → 2-Ethoxy-4-(3-((S)-3-methy-1-(2-piperidin-1-yl-phenyl)-butylamino)-2-oxo-propyl)-benzoic acid ethyl ester

HRID 1857026
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HRID 1857026 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:15][C:16]([OH:18])=O)[CH:7]=[CH:8][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2].[CH3:19][CH:20]([CH3:36])[CH2:21][C@H:22]([NH2:35])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:15][C:16]([NH:35][C@H:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)[CH2:21][CH:20]([CH3:36])[CH3:19])=[O:18])[CH:7]=[CH:8][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10868Dicyclohexylcarbodiimide2회HCID 101312123-Ethoxy-4-ethoxycarbonylphenylacetic acid2회HCID 105146093-Methyl-1-(2-piperidinophenyl)-1-butylamine, (S)-

생성물 1

HCID 106484192-Ethoxy-4-(3-((S)-3-methy-1-(2-piperidin-1-yl-phenyl)-butylamino)-2-oxo-propyl)-benzoic acid ethyl ester

시약·촉매·용매 1

HCID 1140
Toluene
용매
2회

실험 절차

2.77 g (11 mMol) of 3-ethoxy-4-ethoxycarbonyl-phenylacetic acid are added at ambient temperature to a solution of 2.71 g (11 mMol) of anhydrous (S)-3-methyl-1-(2-piperidino-phenyl)-1-butylamine (ee=98.5%) in 30 ml of absolute toluene and the mixture is stirred until dissolved. Then 2.38 g (11.55 mMol) of N,N'-dicyclohexyl-carbodiimide are added and the mixture is stirred at ambient temperature. After 24 hours a further 0.54 g (2.14 mMol) of 3-ethoxy-4-ethoxycarbonyl-phenylacetic acid and 0.48 g (2.33 mMol) of N,N'-dicyclohexylcarbodiimide are added and the mixture is stirred overnight. It is then cooled to an internal temperature of +5° C. and suction filtered to separate the precipitate, which is washed once with 5 ml of toluene. The combined toluene filtrates are evaporated down in vacuo to a volume of about 10 ml. The resulting solution is heated over the steam bath and petroleum ether is added in batches thereto (total of 55 ml) until the turbidity remains. It is cooled in ice, whereupon crystallisation takes place. It is suction filtered and dried at 75° C./4 torr. The product obtained (4.57 g; melting point 111-112° C.; ee=98.9%) is suspended in 50 ml of petroleum ether. The mixture is heated over the steam bath and sufficient toluene is added in batches (8 ml in total) until a solution is obtained. This is then cooled in ice and suction filtered to separate the crystals, which are dried at 75° C./4 torr.

후처리

  1. dissolutionuntil dissolved
  2. stirringthe mixture is stirred at ambient temperature
  3. stirringthe mixture is stirred overnight
  4. temperatureIt is then cooled to an internal temperature of +5° C. and suction
  5. filtrationfiltered
  6. customto separate the precipitate, which
  7. washis washed once with 5 ml of toluene
  8. customThe combined toluene filtrates are evaporated down in vacuo to a volume of about 10 ml
  9. temperatureThe resulting solution is heated over the steam bath and petroleum ether
  10. additionis added in batches
  11. temperatureIt is cooled in ice, whereupon crystallisation
  12. filtrationfiltered
  13. customdried at 75° C./4 torr
  14. customThe product obtained (4.57 g; melting point 111-112° C.; ee=98.9%)
  15. additionis added in batches (8 ml in total) until a solution
  16. customis obtained
  17. temperatureThis is then cooled in ice
  18. filtrationsuction filtered
  19. customto separate the crystals, which
  20. customare dried at 75° C./4 torr

출처 및 근거

ORD 기록
ord-5aa0dd87ff5e42f09f89253460281537
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06143769

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