Water → (4-(6,7-Bis(myristyloxy)-4-thiaheptanoylamino)benzoyl)glutamic acid di-t-butyl ester

HRID 1720817

반응식

HRID 1720817 반응식
[C:1]([O:5][C:6](=[O:37])[C@H:7]([CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:8][C:9](=[O:27])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:26])[CH2:18][CH2:19][S:20][CH2:21][CH:22]([OH:25])[CH2:23][OH:24])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].CN([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43]N=1)C.O>C(Cl)(Cl)Cl.C(N(CC)CC)C.C(Cl)CCCCCCCCCCCCC>[C:1]([O:5][C:6](=[O:37])[C@H:7]([CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[NH:8][C:9](=[O:27])[C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:26])[CH2:18][CH2:19][S:20][CH2:21][CH:22]([O:25][CH2:43][CH2:44][CH2:45][CH2:46][CH2:41][CH2:43][CH2:44][CH2:45][CH2:46][CH2:41][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:23][O:24][CH2:41][CH2:46][CH2:45][CH2:44][CH2:43][CH2:43][CH2:44][CH2:45][CH2:46][CH2:41][CH2:6][CH2:7][CH2:28][CH3:29])=[CH:14][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 3

HCID 962WaterHCID 218852-DimethylaminopyridineHCID 10602544HCID 10602544, 화합물

생성물 1

HCID 54092033(4-(6,7-Bis(myristyloxy)-4-thiaheptanoylamino)benzoyl)glutamic acid di-t-butyl ester수율 85%

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 8471Triethylamine용매HCID 17043Myristyl chloride용매

실험 절차

To a solution of (4-(6,7-dihydroxy-4-thiaheptanoylamino)benzoyl)glutamic acid di-t-butyl ester as obtained in Reference Example 6 (50 mg) in chloroform (1 ml), triethylarnine (0.258 ml), myristyl chloride (0.196 ml) and dimethylaminopyridine (1 mg) were added, followed by stirring at room temperature for 24 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with a 5% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to yield the title compound (76 mg, yield 85%) as a wax-like substance.

후처리

  1. additionwere added
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with a 5% aqueous solution of citric acid
  4. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-573602f9fd0244a08cdfb5e46d8d96da
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05506267

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