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Water → (6,7-Bis(palmitoyloxy)-4-thiaheptanoyl)glycylglycylglycine t-butyl ester

HRID 1720810
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HRID 1720810 반응식
[C:1]([O:18][CH:19]([CH2:27][O:28][C:29](=[O:45])[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][CH2:43][CH3:44])[CH2:20][S:21][CH2:22][CH2:23][C:24]([OH:26])=O)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl.[C:47]([O:51][C:52](=[O:63])[CH2:53][NH:54][C:55](=[O:62])[CH2:56][NH:57][C:58](=[O:61])[CH2:59][NH2:60])([CH3:50])([CH3:49])[CH3:48].P(C#N)(OCC)(OCC)=O.O>CN(C)C=O.C(N(CC)CC)C>[C:47]([O:51][C:52](=[O:63])[CH2:53][NH:54][C:55](=[O:62])[CH2:56][NH:57][C:58](=[O:61])[CH2:59][NH:60][C:24](=[O:26])[CH2:23][CH2:22][S:21][CH2:20][CH:19]([O:18][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:27][O:28][C:29](=[O:45])[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][CH2:43][CH3:44])([CH3:50])([CH3:48])[CH3:49]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 76257Diethyl cyanophosphonateHCID 105562786,7-Bis(palmitoyloxy)-4-thiaheptanoic acidHCID 86749435Glycylglycylglycine t-butyl ester hydrochloride

생성물 1

HCID 22418631(6,7-Bis(palmitoyloxy)-4-thiaheptanoyl)glycylglycylglycine t-butyl ester수율 20%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8471Triethylamine용매

실험 절차

To a solution of 6,7-bis(palmitoyloxy)-4-thiaheptanoic acid as obtained in Reference Example 4 (400 mg) and glycylglycylglycine t-butyl ester hydrochloride (149 mg) in dimethylformamide (6 ml), triethylamine (0.094 ml) and diethyl cyanophosphate (150 mg) were added at 0° C., followed by stirring at room temperature for 1 hour. After addition of water, the reaction mixture was extracted with chloroform. 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 recrystallized (acetone-hexane) to yield the title compound (110 mg, yield 20%) as a wax-like substance.

후처리

  1. additionwere added at 0° C.
  2. extractionthe reaction mixture was extracted with chloroform
  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 recrystallized (acetone-hexane)

출처 및 근거

ORD 기록
ord-f9bc5c355655454f9f491e3486211712
출처 데이터셋
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05506267

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