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4-Quinolinecarboxylic acid → N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-[(4-quinolinylcarbonyl)amino]-L-phenylalanine

HRID 1282599
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HRID 1282599 반응식
C[O:2][C:3](=[O:30])[C@H:4]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1)[NH:5][C:6]([C:8]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[N:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([C:41](O)=[O:42])=[CH:33][CH:32]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[OH-].[Na+]>CN(C=O)C.C(OCC)(=O)C.CCOCC.CO>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C:8]2([C:6]([NH:5][C@H:4]([C:3]([OH:2])=[O:30])[CH2:22][C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:41]([C:34]4[C:35]5[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=5)[N:31]=[CH:32][CH:33]=4)=[O:42])=[CH:25][CH:24]=3)=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:19][CH:18]=1
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참가 물질

10

반응물 5

HCID 102434-Quinolinecarboxylic acidHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 544852054-Amino-N-[[1[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine methyl ester

생성물 1

HCID 11157112
N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-[(4-quinolinylcarbonyl)amino]-L-phenylalanine
수율 55.1%

시약·촉매·용매 4

HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-amino-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine methyl ester (30.7 mg, 0.075 mmol), quinoline-4-carboxylic acid (17 mg, 0.10 mmol), and HBTU (38 mg, 0.10 mmol) in 1 mL of DMF was treated with diisopropylethylamine (30 μL, 0.17 mmol). The mixture was stirred over night and was diluted with 15 mL of ethyl acetate and 10 mL of ether and was washed with water (2×10 mL), saturated NaHCO3 (1×10 mL) and was dried (MgSO4). Concentration gave 42 mg which was dissolved in 3 mL of methanol. Sodium hydroxide (0.10 mL, 4 N, 0.4 mmol) was added and the mixture was stirred for 2 hours. The excess base was quenched by addition of acetic acid (0.1 mL), the solution was filtered through a 0.2μ nylon filter and the filtrate was purified by RP-HPLC on a 4×30 cm Rainin C-18 column using a gradient of 5 to 95% acetonitrile:water containing 0.75% trifluoroacetic acid at a flow of 49 mL/min over 30 min. The peak eluting at 74% acetonitrile was concentrated and lyophilized to give N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-[(4-quinolinylcarbonyl)amino]-L-phenylalanine (22.8 mg), HR-FAB-MS: obs. mass 552.2482. Calcd. mass 552.2498 (M+H). The peak eluting at 82.6% acetonitrile was recovered N-[[1-[(4-methoxyphenyl)methyl]cyclopentylcarbonyl]-4-[(4-quinolinylcarbonyl)amino]-L-phenylalanine methyl ester (11.2 mg), HR-FAB-MS: obs. mass 566.2675. Calcd. mass 566.2655 (M+H).

후처리

  1. washwas washed with water (2×10 mL), saturated NaHCO3 (1×10 mL)
  2. dry with materialwas dried (MgSO4)
  3. concentrationConcentration
  4. customgave 42 mg which
  5. stirringthe mixture was stirred for 2 hours
  6. customThe excess base was quenched by addition of acetic acid (0.1 mL)
  7. filtrationthe solution was filtered through a 0.2μ nylon
  8. filtrationfilter
  9. customthe filtrate was purified by RP-HPLC on a 4×30 cm Rainin C-18 column
  10. washThe peak eluting at 74% acetonitrile
  11. concentrationwas concentrated

출처 및 근거

ORD 기록
ord-11d58fe42e77476f98d7c996fad8f5bf
출처 데이터셋
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06455550B1

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