Hydrochloric Acid → HCID 10803968、化合物

HRID 1004660ノート

反応式

HRID 1004660 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[O:28]([CH2:35][CH2:36][CH2:37][NH2:38])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>O1CCCC1.[Cl-].[Na+].O>[O:28]([CH2:35][CH2:36][CH2:37][NH:38][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 739273-(p-Tolyl)propionic acidHCID 418237(3-Phenoxypropyl)amine

生成物 1

HCID 10803968HCID 10803968、化合物収率 61%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of 4-methylbenzenepropanoic acid (2.0 g, 12.2 mmol) and triethylamine (4.3 mL, 3.1 g, 30.9 mmol) in 80 mL of tetrahydrofuran is cooled in ice and treated dropwise with isobutyl chloroformate (1.7 mL, 1.8 g, 13.1 mmol). The mixture is stirred for 1 hour, and a solution of 3-phenoxy-1-propanamine (1.9 g, 12.6 mmol) in 10 mL of tetrahydrofuran is added slowly. The mixture is stirred at room temperature for 18 hours, then added to 400 mL of brine. The mixture is acidified with 4.0 N hydrochloric acid and extracted with ethyl acetate. The combined organic layers are washed with brine, dried (anhydrous sodium sulfate), and evaporated. Recrystallization of the residue gives 2.2 g (61%) of the amide intermediate product, mp 101-102° C.

後処理

  1. stirringThe mixture is stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. customevaporated
  6. customRecrystallization of the residue

出典と根拠

ORDレコード
ord-79cf617ba86e4854be7b9e82ccf85aa8
出典データセット
uspto-grants-2000_04
特許番号
US06051605

反応ノート

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