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Hydrochloric Acid → 2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxyphenyl)-ethyl]-4-phenyl-butyramide

HRID 1818652
ノート
印刷プレビュー

反応式

HRID 1818652 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][NH:15][CH:16]=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]#[CH:12].C(N(CC)CC)C.C(=O)(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[C:37]1([CH2:43][CH2:44][CH:45]=[O:46])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[OH:46][CH:45]([CH2:44][CH2:43][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:16]([NH:15][CH2:14][CH2:13][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]#[CH:12])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:17]
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

8

反応物 5

HCID 313Hydrochloric AcidHCID 7707BenzenepropanalHCID 8471TriethylamineHCID 94429TriphosgeneHCID 11379286Formamide, N-[2-[3-methoxy-4-(2-propynyloxy)phenyl]ethyl]-

生成物 1

HCID 578850672-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxyphenyl)-ethyl]-4-phenyl-butyramide

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒4 回

反応条件

温度
-78 °C

実験手順

N-[2-(3-Methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-formamide (8.0 g, 34 mmol) and triethylamine (8.3 g, 82 mmol) are dissolved in dichloromethane (80 ml). Bis(trichloromethyl) carbonate (triphosgene, 4.0 g, 14 mmol) in dichloromethane (40 ml) is added at +5° C. The mixture is stirred for 4 hours at +5° C. and then cooled to −78° C. A solution of titanium tetrachloride (7.0 g, 38 mmol) in dichloromethane (70 ml) is added and the mixture is stirred for 2 hours at −40° C. 3-Phenylpropionaldehyde (4.8 g, 36 mmol) in dichloromethane (50 ml) is added dropwise and the mixture is stirred for 17 hours at room temperature. The mixture is hydrolysed with 5N HCl (25 ml), stirred 30 minutes at room temperature and washed with water. After evaporation of the organic layer the residue is submitted to flash-chromatography (ethyl acetate/hexane 6:3) to give 2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxyphenyl)-ethyl]-4-phenyl-butyramide (Compound E1.01).

後処理

  1. stirringthe mixture is stirred for 2 hours at −40° C
  2. stirringthe mixture is stirred for 17 hours at room temperature
  3. stirringstirred 30 minutes at room temperature
  4. washwashed with water
  5. customAfter evaporation of the organic layer the residue

出典と根拠

ORDレコード
ord-63e648549493420c9fbcc536df3700c5
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07601674B2

反応ノート

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