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Triethylamine → BOC-p-nitrophenylalanine 2-oxopropyl amide

HRID 2372573
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HRID 2372573 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:24][CH2:25][C:26](=[O:28])[CH3:27].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.C(O)(=O)C>[O:28]=[C:26]([CH3:27])[CH2:25][NH:24][C:20](=[O:22])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 30840252-Propanone, 1-amino-, hydrochlorideHCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

생성물 1

HCID 18632424BOC-p-nitrophenylalanine 2-oxopropyl amide

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매2회

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온도
0 °C

실험 절차

t-Butyloxycarbonyl-p-nitrophenylalanine (4.42g, 14.26 mmol, aminoacetone hydrochloride (1.56 g, 14.26 mmol), triethylamine (1.44 g, 14.26 mmol), 1-hydroxybenzotriazole (1.69 g, 12.55 mmol), were dissolved in ethyl acetate (400 ml). 1,3-Dicyclohexylcarbodiimide (3.23 g, 15.68 mmol) in ethyl acetate (25 ml) was added and the solution allowed to stir for 18 hours. Glacial acetic acid (0.2 ml) was added and the solution was filtered. The filtrate was extracted with saturated salt solution (100 ml), lN HCl solution (3×100 ml), and saturated salt solution (100 ml), 5% bicarbonate solution (3×100 ml), and saturated salt solution (100 ml). The organic phase was dried over MgSO4 , filtered and concentrated to 50 ml. Petroleum ether (50 ml) was added and the solution was cooled to 0° C. for 12 hours. The precipitated product was collected and dried under vacuum.

후처리

  1. filtrationthe solution was filtered
  2. extractionThe filtrate was extracted with saturated salt solution (100 ml), lN HCl solution (3×100 ml), and saturated salt solution (100 ml), 5% bicarbonate solution (3×100 ml), and saturated salt solution (100 ml)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to 50 ml
  6. additionPetroleum ether (50 ml) was added
  7. customThe precipitated product was collected
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-c98996705224496485137af2027e84e9
출처 데이터셋
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05099069

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