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Dichloromethane → tert-Butyl ((1S,2R)-1-benzyl-2-hydroxy-3-(isobutyl((4-nitrophenyl)sulfonyl)amino)propyl)carbamate

HRID 1505572
ノート
印刷プレビュー

反応式

HRID 1505572 の反応式
[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:9]([OH:16])[CH2:10][NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)Cl.[N+:35]([C:38]1[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1)([O-:37])=[O:36]>O>[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C@H:9]([OH:16])[CH2:10][N:11]([S:44]([C:41]1[CH:40]=[CH:39][C:38]([N+:35]([O-:37])=[O:36])=[CH:43][CH:42]=1)(=[O:45])=[O:46])[CH2:12][CH:13]([CH3:14])[CH3:15])([CH3:3])([CH3:4])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 9902339tert-Butyl ((2S,3R)-3-hydroxy-4-((2-methylpropyl)amino)-1-phenylbutan-2-yl)carbamate

生成物 1

HCID 10279676tert-Butyl ((1S,2R)-1-benzyl-2-hydroxy-3-(isobutyl((4-nitrophenyl)sulfonyl)amino)propyl)carbamate収率 93.5%

試薬・触媒・溶媒

1
HCID 962Water溶媒

反応条件

温度
42.5 °C

実験手順

[(1S,2R)-3-[(2-methylpropyl)amino]-2-hydroxy-1-(phenyl methyl)propyl]carbamic acid tert-butyl ester (4, 100 gm) and triethylamine (39.04 g) was added to methylenedichloride (1200 mL) and the temperature was raised to 40° C. p-nitro benzene sulfonyl chloride solution (72.3 g of p-NBSC dissolve in 300 mL methylenedichloride) was added slowly at 40-45° C. for 2-3 hrs. The reaction was maintained for 3 hours at 40-45° C. After completion of the reaction, water (500 mL) was added, separated the organic layer and distilled out methylene dichloride at atmospheric pressure. Finally, strip out the methylene dichloride by using isopropyl alcohol (200 mL). Isopropyl alcohol (1000 mL) was added to the distillate and maintained the stirring for 60 minutes at 70-80° C. Cooled the mass to 30-35° C., filtered and washed with Isopropyl alcohol to get title compound 3 (yield 145 g).

後処理

  1. additionwas added slowly at 40-45° C. for 2-3 hrs
  2. additionwas added
  3. customseparated the organic layer
  4. distillationdistilled out methylene dichloride at atmospheric pressure
  5. additionIsopropyl alcohol (1000 mL) was added to the distillate
  6. temperaturemaintained the stirring for 60 minutes at 70-80° C
  7. temperatureCooled the mass to 30-35° C.
  8. filtrationfiltered
  9. washwashed with Isopropyl alcohol

出典と根拠

ORDレコード
ord-29f8020d0da140b6b0a79a4e1fb17dd9
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09216990B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート