Triethylamine → 2-(2-Hydroxy-3-methyl-butyrylamino)-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide

HRID 852343ノート

反応式

HRID 852343 の反応式
[OH:1][C@@H:2]([CH:6]([CH3:8])[CH3:7])[C:3](O)=[O:4].[C:9]([C:13]1[S:17][C:16]([NH:18][C:19](=[O:25])[CH:20]([NH2:24])[CH2:21][CH2:22][CH3:23])=[N:15][N:14]=1)([CH3:12])([CH3:11])[CH3:10].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>C(Cl)Cl>[C:9]([C:13]1[S:17][C:16]([NH:18][C:19](=[O:25])[CH:20]([NH:24][C:3](=[O:4])[CH:2]([OH:1])[CH:6]([CH3:8])[CH3:7])[CH2:21][CH2:22][CH3:23])=[N:15][N:14]=1)([CH3:11])([CH3:10])[CH3:12]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 853180(S)-2-Hydroxy-3-methylbutanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 860331642-Amino-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide

生成物 1

HCID 116101072-(2-Hydroxy-3-methyl-butyrylamino)-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2-(S)-hydroxyl-3-methyl-butyric acid (35.4 mg, 0.3 mmol), 2-amino-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide (88 mg, 0.3 mmol), HBOT (43 mg, 0.21 mmol), EDC HCl (69 mg, 0.36 mmol.) and triethylamine (0.17 ml) in 2 ml of methylene chloride was stirred at room temperature until product formation or disappearance of starting material. The mixture was quenched with water and extracted with methylene chloride. The organic layer was separated, washed with dilute HCl, brine, dried over sodium sulfate and the solvent was removed at reduced pressure to provide the title compound as a cude oil. The oil was purified by Shimadzu HPLC to provide the title compound as a light yellow solid (44 mg), LC-MS M+1=357.1

後処理

  1. customThe mixture was quenched with water
  2. extractionextracted with methylene chloride
  3. customThe organic layer was separated
  4. washwashed with dilute HCl, brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed at reduced pressure

出典と根拠

ORDレコード
ord-feac8b54abc447ae8ec7e3c95e57ef45
出典データセット
uspto-grants-2007_08
特許番号
US07253195B2

反応ノート

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