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

HRID 1720810
ノート
印刷プレビュー

反応式

HRID 1720810 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f9bc5c355655454f9f491e3486211712
出典データセット
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05506267

反応ノート

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