Dimethylformamide → (3-{(1r)-1-[(1r)-1-(3-Methyl-[1,2,4]oxadiazol-5-yl)-2-phenylethylcarbamoyl]-2-(2-naphthyl)ethylcarbamoyl}-benzyl)carbamic acid tertbutyl ester

HRID 1701020노트

반응식

HRID 1701020 반응식
Cl.CN(C)CCCN=C=NCC.O.ON1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1.[C:24]([O:28][C:29]([NH:31][C:32]1C=C(C=CC=1)C(O)=O)=[O:30])([CH3:27])([CH3:26])[CH3:25].Cl.[NH2:42][C@H:43]([CH2:61][C:62]1[CH:71]=[CH:70][C:69]2[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=2)[CH:63]=1)[C:44]([NH:46][C@@H:47]([C:55]1[O:59][N:58]=[C:57]([CH3:60])[N:56]=1)[CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:45].C(N(CC)CC)C.CN(C)[CH:81]=[O:82]>>[C:24]([O:28][C:29](=[O:30])[NH:31][CH2:32][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:81](=[O:82])[NH:42][C@@H:43]([C:44](=[O:45])[NH:46][C@@H:47]([C:55]2[O:59][N:58]=[C:57]([CH3:60])[N:56]=2)[CH2:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH2:61][C:62]2[CH:71]=[CH:70][C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[CH:63]=2)[CH:19]=1)([CH3:27])([CH3:25])[CH3:26]

참가 물질

7

반응물 6

HCID 6228Dimethylformamide2회HCID 8471TriethylamineHCID 8541623-(((Tert-butoxy)carbonyl)amino)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69834587(2R)-2-amino-N-[(1R)-1-(3-methyl-[1,2,4]oxadiazol-5-yl)-2-phenylethyl]-3-(2-naphthyl)propionamide hydrochloride

생성물 1

HCID 53665347(3-{(1r)-1-[(1r)-1-(3-Methyl-[1,2,4]oxadiazol-5-yl)-2-phenylethylcarbamoyl]-2-(2-naphthyl)ethylcarbamoyl}-benzyl)carbamic acid tertbutyl ester

실험 절차

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.92 g, 4.82 mmol) and 1-hydroxybenzotriazole monohydrate (0.74 g, 4.83 mmol) were added to a solution of N-tertbutoxycarbonyl-3-aminobenzoic acid (1.21 g, 4.82 mmol) in N,N-dimethylformamide (15 ml). After 1 h at 20° C. a mixture of (2R)-2-amino-N-[(1R)-1-(3-methyl-[1,2,4]oxadiazol-5-yl)-2-phenylethyl]-3-(2-naphthyl)propionamide hydrochloride (1.50 g, 3.43 mmol) and triethylamine (0.35 g, 3.46 mmol) in N,N-dimethylformamide (15 ml) were added. After 18 h at 20° C. the reaction mixture was poured on ice water (180 ml) and extracted several times with dichloromethane (total 180 ml). The organic phases were collected and washed with aqueous citric acid (10%, 25 ml), a saturated solution of sodium hydrogencarbonate (3×25 ml) and water (3×25 ml). After drying (magnesium sulfate) the solution was concentrated in vacuo and 1.80 g of (3-{(1R)-1-[(1R)-1-(3-methyl-[1,2,4]oxadiazol-5-yl)-2-phenylethylcarbamoyl]-2-(2-naphthyl)ethylcarbamoyl}-benzyl)carbamic acid tertbutyl ester was isolated from ethyl acetate.

후처리

  1. additionwere added
  2. additionAfter 18 h at 20° C. the reaction mixture was poured on ice water (180 ml)
  3. extractionextracted several times with dichloromethane (total 180 ml)
  4. customThe organic phases were collected
  5. washwashed with aqueous citric acid (10%, 25 ml)
  6. dry with materialAfter drying (magnesium sulfate) the solution
  7. concentrationwas concentrated in vacuo

출처 및 근거

ORD 기록
ord-67f2c86482474a65b7700c36faf65fa1
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350767B1

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