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Water → (4-(6,7-Bis(palmitoyloxy)-2-methyl-4-thiaheptanoyl)amino-benzoyl)glutamic acid di-t-butyl ester

HRID 1720836
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HRID 1720836 반응식
[C:1]([O:5][C:6](=[O:27])[C@H:7]([CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[C:28]([O:45][CH:46]([CH2:55][O:56][C:57](=[O:73])[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])[CH2:47][S:48][CH2:49][CH:50]([CH3:54])[C:51](O)=[O:52])(=[O:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].O>N1C=CC=CC=1.P(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:27])[C@H:7]([CH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:51](=[O:52])[CH:50]([CH3:54])[CH2:49][S:48][CH2:47][CH:46]([O:45][C:28](=[O:44])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:55][O:56][C:57](=[O:73])[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])=[CH:12][CH:11]=1)([CH3:3])([CH3:4])[CH3:2]
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참가 물질

6

반응물 3

HCID 962WaterHCID 105324766,7-Bis(palmitoyloxy)-2-methyl-4-thiaheptanoic acidHCID 10691066L-Glutamic acid, N-(4-aminobenzoyl)-, bis(1,1-dimethylethyl) ester

생성물 1

HCID 10701254(4-(6,7-Bis(palmitoyloxy)-2-methyl-4-thiaheptanoyl)amino-benzoyl)glutamic acid di-t-butyl ester수율 62%

시약·촉매·용매 2

HCID 1049
Pyridine
용매
HCID 24387Phosphorus trichloride용매

실험 절차

To a solution of 4-aminobenzoylglutamic acid di-t-butyl ester (378 mg) in pyridine (5 ml), phosphorus trichloride (0.044 ml) was added, followed by stirring at room temperature for 2 hours. To this solution, 6,7-bis(palmitoyloxy)-2-methyl-4-thiaheptanoic acid as obtained in Reference Example 42 (336 mg) was 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 (315 mg, yield 62%) as a wax-like substance.

후처리

  1. additionwas added
  2. stirringby stirring at room temperature for 24 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with a 5% aqueous solution of citric acid
  5. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate =2:1)

출처 및 근거

ORD 기록
ord-e8e5ecff5b0c448c8aa628bf484d181f
출처 데이터셋
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05506267

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