Triethylamine → benzyl 4-(3-cyanophenoxy)-3-(3R)-[4-(pyrrolidine-1-carbonyl)benzoylamino]butyrate

HRID 747784ノート

反応式

HRID 747784 の反応式
Cl.[NH2:2][C@@H:3]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=1)[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[N:54]1([C:59]([C:61]2[CH:69]=[CH:68][C:64]([C:65](O)=[O:66])=[CH:63][CH:62]=2)=[O:60])[CH2:58][CH2:57][CH2:56][CH2:55]1>ClCCl>[C:23]([C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][CH2:15][C@H:3]([NH:2][C:65](=[O:66])[C:64]1[CH:63]=[CH:62][C:61]([C:59]([N:54]2[CH2:58][CH2:57][CH2:56][CH2:55]2)=[O:60])=[CH:69][CH:68]=1)[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])#[N:24]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10932939Benzoic acid, 4-(1-pyrrolidinylcarbonyl)-HCID 86760704benzyl (3R)-3-amino-4-(3-cyanophenoxy)butyrate hydrochloride

生成物 1

HCID 68832164benzyl 4-(3-cyanophenoxy)-3-(3R)-[4-(pyrrolidine-1-carbonyl)benzoylamino]butyrate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1.8 g (5.2 mmol) of benzyl (3R)-3-amino-4-(3-cyanophenoxy)butyrate hydrochloride (the compound in step 2 in Example 52), 703 mg (5.2 mmol) of 1-hydroxybenzotriazole (hydrate), 997 mg (5.2 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride, 526 mg (5.2 mmol) of triethylamine, and 1.14 g (5.2 mmol) of 4-(1-pyrrolidyl carbonyl)benzoic acid were stirred in dichloromethane overnight. The reaction solution was washed with 1 N hydrochloric acid, 1 N aqueous sodium hydroxide and saturated saline and dried over sulfate magnesium anhydride, and the solvent was distilled off. The resulting residue was purified by silica gel chromatography (ethyl acetate) to obtain the title compound.

後処理

  1. washThe reaction solution was washed with 1 N hydrochloric acid, 1 N aqueous sodium hydroxide and saturated saline
  2. dry with materialdried over sulfate magnesium anhydride
  3. distillationthe solvent was distilled off
  4. customThe resulting residue was purified by silica gel chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-bf80ac5879e1489fa5675e869d7f03b5
出典データセット
uspto-grants-2008_07
特許番号
US07396844B1

反応ノート

読み込み中…