4-Methylmorpholine → diethyl (2S)-2-[[4-[1-(2-acetamido-4-oxo-1H-pyrido[2,3-d]pyrimidin-6-yl)prop-1-en-2-yl]benzoyl]amino]pentanedioate

HRID 231299노트

반응식

HRID 231299 반응식
[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:27])[C:8]2[CH:14]=[C:13]([CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24](O)=[O:25])=[CH:20][CH:19]=3)[CH3:17])[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2].CN1CCOCC1.C1(NP(Cl)(=O)OC2C=CC=CC=2)C=CC=CC=1.[NH2:52][C@H:53]([C:61]([O:63][CH2:64][CH3:65])=[O:62])[CH2:54][CH2:55][C:56]([O:58][CH2:59][CH3:60])=[O:57]>CN1CCCC1=O>[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:27])[C:8]2[CH:14]=[C:13]([CH:15]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([C:24]([NH:52][C@H:53]([C:61]([O:63][CH2:64][CH3:65])=[O:62])[CH2:54][CH2:55][C:56]([O:58][CH2:59][CH3:60])=[O:57])=[O:25])=[CH:22][CH:23]=3)[CH3:17])[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 73961Glutamic acid diethyl esterHCID 103959Phosphoramidochloridic acid, N-phenyl-, phenyl esterHCID 178474469HCID 178474469, 화합물

생성물 1

HCID 178471565diethyl (2S)-2-[[4-[1-(2-acetamido-4-oxo-1H-pyrido[2,3-d]pyrimidin-6-yl)prop-1-en-2-yl]benzoyl]amino]pentanedioate

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a solution of 0.2 g of 2-acetamido-4-hydroxy-6-[2-(4-carboxyphenyl)prop-1-enyl]pyrido[2,3-d]pyrimidine in 50 mL of N-methylpyrrolidinone containing 0.18 g of N-methylmorpholine was added 0.22 g of phenyl N-phenylphosphoramidochloridate in a single portion. After stirring the mixture at room temperature for 1 hour, 0.20 g of diethyl L-glutamate was added. The reaction mixture was stirred overnight, the solvent was removed under reduced pressure and the residue was triturated with chloroform. The mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was subjected to preparative thin layer chromatography on silica gel using a 5% methanol in chloroform mixture as the eluent. This gave 74.6 mg (25%) of the title compound as a pale yellowish solid; NMR (CDCl3, 250 MHz) d 1.22 (t, 3H, J=7.1 Hz), 1.30 (t, 3H J=7.1 Hz), 2.11-2.57 (m, 10H), 4.14 (q, 2H, J=7.1 Hz), 4.24 (q, 2H, J=7.1 Hz), 4.75-4.83 (m, 1H), 6.86 (brs, 1H), 7.18 (brs, 1 H), 7.57 (d, 2H, J=8.42 Hz), 7.84 (d, 2H, J=8.42 Hz), 8.50 (d, 1H, J=2.01 Hz), 8.96 (brs, 1H), 10.34 (brs, 1H).

후처리

  1. stirringThe reaction mixture was stirred overnight
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was triturated with chloroform
  4. filtrationThe mixture was filtered
  5. customthe filtrate was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-f0ddd0d52dd04758a2e543bb55ffec42
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845216

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