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

HRID 852343노트

반응식

HRID 852343 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-feac8b54abc447ae8ec7e3c95e57ef45
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253195B2

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