Dicyclohexylcarbodiimide → (1S,2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(3,3-diethoxypropyl)amino]-1-methyl-3-oxopropyl myristate

HRID 25706

反応式

HRID 25706 の反応式
[CH2:1]([O:8][C:9](=[O:27])[NH:10][C@H:11]([C:15](=[O:26])[NH:16][CH2:17][CH2:18][CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])[C@@H:12]([OH:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](O)(=[O:42])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:28]([O:14][C@@H:12]([CH3:13])[C@H:11]([NH:10][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:27])[C:15]([NH:16][CH2:17][CH2:18][CH:19]([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25])=[O:26])(=[O:42])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 11005Myristic AcidHCID 218852-DimethylaminopyridineHCID 69752191[(1S,2S)-1-(3,3-diethoxy-propylcarbamoyl)-2-hydroxy-propyl]-carbamic acid benzyl ester

生成物 1

HCID 69752788(1S,2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(3,3-diethoxypropyl)amino]-1-methyl-3-oxopropyl myristate収率 83.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of [(1S,2S)-1-(3,3-diethoxy-propylcarbamoyl)-2-hydroxy-propyl]carbamic acid benzyl ester (300 mg, 0.785 mmol, obtained from Reference Example 17) in methylene chloride (5 ml) was added myristic acid (163 mg, 0.714 mmol), dicyclohexylcarbodiimide (162 mg, 0.785 mmol) and dimethylaminopyridine (9 mg, 0.074 mmol). The resulting mixture was stirred under nitrogen at room temperature for 18 hours. The mixture was filtered, the filtrate was washed with 2% hydrochloric acid, aqueous sodium bicarbonate and saturated sodium chloride solutions, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (flash column, silica gel, 30% ethyl acetate in hexane) to provide (1S,2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(3,3-diethoxypropyl)amino]-1-methyl-3-oxopropyl myristate (352 mg, 83%) as a white solid.

後処理

  1. filtrationThe mixture was filtered
  2. washthe filtrate was washed with 2% hydrochloric acid, aqueous sodium bicarbonate and saturated sodium chloride solutions
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed (flash column, silica gel, 30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-c242901b55274e3d957cc8d1f24cfea8
出典データセット
uspto-grants-2005_02
特許番号
US06858591B2

関連ノート

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