Morpholine → Tert-butyl 4-(morpholinomethyl)thiazol-2-ylcarbamate

HRID 520488

反応式

HRID 520488 の反応式
O[CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[S:6][CH:7]=1.CCN(CC)CC.CS(Cl)(=O)=O.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>C(Cl)Cl>[O:31]1[CH2:32][CH2:33][N:28]([CH2:2][C:3]2[N:4]=[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[S:6][CH:7]=2)[CH2:29][CH2:30]1

参加物

6

反応物 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22280475(4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester

生成物 1

HCID 58154672Tert-butyl 4-(morpholinomethyl)thiazol-2-ylcarbamate収率 72.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

tert-Butyl 4-(hydroxymethyl)thiazol-2-ylcarbamate 89 (2.00 g, 8.68 mmol) was taken up in 25 mL of CH2Cl2 along with Et3N (1.82 mL, 13.05 mmol) and cooled to 0° C. Methanesulfonyl chloride (0.85 mL, 10.88 mmol) was added and the resulting reaction mixture was stirred at 0° C. for 60 min. Morpholine 63 (3.0 mL, 35 mmol) was then added and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure. The resulting residue was taken up in EtOAc and washed with dilute aqueous NaHCO3, brine, dried with Na2SO4, and concentrated under reduced pressure. This material was purified by filtering through a short column of silica gel. The filtrate was concentrated to afford 90 (1.88 g, 69% yield).

後処理

  1. customthe resulting reaction mixture
  2. stirringthe reaction mixture was stirred at room temperature for 18 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washwashed with dilute aqueous NaHCO3, brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThis material was purified
  8. filtrationby filtering through a short column of silica gel
  9. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-ded2a1763b7646699b6e7d47fecf5e4c
出典データセット
uspto-grants-2016_05
特許番号
US09326986B2

関連ノート

読み込み中…