Palmitic Acid → 9-(1,3-Di-n-hexadecanoyloxy-2-propoxymethyl)guanine

HRID 1655342

반응식

HRID 1655342 반응식
[OH:1][CH2:2][CH:3]([O:6][CH2:7][N:8]1[CH:16]=[N:15][C:14]2[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]1=2)[CH2:4][OH:5].[C:19]([OH:36])(=O)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CN(C)C=O>[C:19]([O:1][CH2:2][CH:3]([O:6][CH2:7][N:8]1[CH:16]=[N:15][C:14]2[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]1=2)[CH2:4][O:5][C:19](=[O:36])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])(=[O:36])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

참가 물질

4

반응물 2

HCID 985Palmitic AcidHCID 135398740Ganciclovir

생성물 1

HCID 1363321569-(1,3-Di-n-hexadecanoyloxy-2-propoxymethyl)guanine수율 97.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To 50 mg of 9-(1,3-dihydroxy-2-propoxymethyl)guanine in 5 ml of N,N-dimethylformamide were added 290 mg dicyclohexycarbodiimide and 300 mg of n-hexadecanoic acid and the solution was stirred at 50° C. for 50 hours. The compound was then precipitated in ice water. The water was extracted with methylene chloride (3×). The combined methylene chloride extracts were concentrated, then purified on preparative silica gel plates developed in 1:9 methanol:methylene chloride to yield 140 mg 9-(1,3-di-n-hexadecanoyloxy-2-propoxymethyl)guanine, m.p. 150°-154° C.

후처리

  1. customThe compound was then precipitated in ice water
  2. extractionThe water was extracted with methylene chloride (3×)
  3. concentrationThe combined methylene chloride extracts were concentrated
  4. custompurified on preparative silica gel plates

출처 및 근거

ORD 기록
ord-adf68a765e214188ac710bbed80606e6
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05250535

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