Acetic Acid → HCID 69732875, 화합물

HRID 2416425노트

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HRID 2416425 반응식
[CH2:1]([N:8]1[C:13]2[N:14]([CH3:27])[C:15](=[O:26])[N:16]([CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([OH:25])[CH3:24])[C:17](=[O:18])[C:12]=2[C:11](=[O:28])[CH:10]=[C:9]1[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:49](O)(=[O:51])[CH3:50].CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:49]([O:25][C@@H:23]([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19][N:16]1[C:17](=[O:18])[C:12]2[C:11](=[O:28])[CH:10]=[C:9]([CH3:29])[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:13]=2[N:14]([CH3:27])[C:15]1=[O:26])(=[O:51])[CH3:50]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 60123474HCID 60123474, 화합물

생성물 1

HCID 69732875HCID 69732875, 화합물수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of (R)-8-benzyl-1,7-dimethyl-3-(5-hydroxyhexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.26 g, 3.18 mmol), triphenylphosphine (2.50 g, 9.52 mmol), acetic acid (0.54 ml, 9.52 mmol) and tetrahydrofuran (20 ml), cooled in an ice bath, was added diethylazodicarboxylate (1.5 ml, 9.5 mmol) dropwise. After stirring at room temperature for 4hours, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate-hexanes to afford (S)-3-(5-acetoxyhexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.2 g, 86% yield) as an oil. 1H NMR (300 MHz, CDCl3) δ 1.20 (d, 3H), 1.30-1.75 (m, 6H), 2.02 (s, 3H), 2.49 (s, 3H), 3.67 (s, 3H), 4.03 (t, 2H), 4.88 (sextet, 1H), 5.30 (s, 2H), 6.56 (s, 1H), 7.30-7.56 (m, 5H).

후처리

  1. temperaturecooled in an ice bath
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate-hexanes

출처 및 근거

ORD 기록
ord-283ccd95c09246eda992ed412020edda
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06825180B2

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