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Pyridine → (S)-2-{acetyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methylbutyric acid

HRID 854655
ノート
印刷プレビュー

反応式

HRID 854655 の反応式
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:11][CH:12]([CH3:44])[C@H:13]([NH:21][CH2:22][C@H:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([O:29][CH2:30][C:31]2[N:32]=[C:33]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)[O:34][C:35]=2[CH3:36])[CH2:24]1)[C:14]([O:16]C(C)(C)C)=[O:15]>ClCCl.O>[C:1]([N:21]([CH2:22][C@H:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([O:29][CH2:30][C:31]2[N:32]=[C:33]([C:37]3[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][CH:42]=3)[O:34][C:35]=2[CH3:36])[CH2:24]1)[C@@H:13]([CH:12]([CH3:44])[CH3:11])[C:14]([OH:16])=[O:15])(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86597944tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyrate

生成物 1

HCID 69240762(S)-2-{acetyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methylbutyric acid

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒
2 回

実験手順

12 μl of acetyl chloride and 22 μl of pyridine are added to 40 mg of tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyrate in 0.5 ml of dichloromethane, and the mixture is stirred at room temperature for 18 h. The solution is then diluted with water and dichloromethane, the aqueous phase is removed and extracted with dichloromethane and the combined phases are dried over MgSO4 and concentrated. The residue is taken up in 0.5 ml of trifluoroacetic acid and allowed to stand at room temperature overnight. The solvent is distilled off completely and the residue is purified by HPLC, which gives 17 mg of (S)-2-{acetyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methylbutyric acid. C26H36N2O5 (456.59); LCMS (ESI): 457.36 (MH+).

後処理

  1. customthe aqueous phase is removed
  2. extractionextracted with dichloromethane
  3. dry with materialthe combined phases are dried over MgSO4
  4. concentrationconcentrated
  5. waitto stand at room temperature overnight
  6. distillationThe solvent is distilled off completely
  7. customthe residue is purified by HPLC, which

出典と根拠

ORDレコード
ord-ff110fff65a849a78a16d274d5843534
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07259177B2

反応ノート

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