Sodium Hydroxide → HCID 44461305、化合物

HRID 63718ノート

反応式

HRID 63718 の反応式
C[O:2][C:3](=[O:36])[C@@H:4]([NH:23][C:24]([C:26]1([CH2:31][CH2:32][N:33]=[N+:34]=[N-:35])[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:22])[C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:21])=[CH:8][CH:7]=1.[OH-].[Na+]>C1COCC1.C(O)C.O>[N:33]([CH2:32][CH2:31][C:26]1([C:24]([NH:23][C@@H:4]([CH2:5][C:6]2[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:22])[C:14]3[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=3[Cl:20])=[CH:10][CH:11]=2)[C:3]([OH:36])=[O:2])=[O:25])[CH2:30][CH2:29][CH2:28][CH2:27]1)=[N+:34]=[N-:35]

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 54226348(S)-2-[[1-(2-azidoethyl)cyclopentanecarbonyl]amino]3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester

生成物 1

HCID 44461305HCID 44461305、化合物収率 93.1%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of (S)-2-[[1-(2-azidoethyl)cyclopentanecarbonyl]amino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester (14.77 g, 27.7 mmol) in THF (200 mL) and ethanol (200 mL) was added aqueous 1.0N sodium hydroxide (150 mL) at room temperature. The mixture was stirred for 15 h at room temperature at which time TLC analysis of the mixture indicated the absence of starting material. Then, it was diluted with water (20 mL) and the THF and ethanol were removed by rotary evaporation and diluted with 100 mL of water and extracted with ether (200 mL) to remove any neutral impurities. The aqueous layer was neutralized with 1N HCl and the resulting white solids were collected by filtration and washed with water and hexanes. After air-drying, 13.37 g (93% yield) of (S)-2-[[1-(2-azidoethyl)cyclopentanecarbonyl]amino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid was obtained as a white solid. ES(+)-HRMS m/e calcd. for C24H25Cl2N5O4 (M+Na)+ 540.1176, obsd. 540.1177.

後処理

  1. customthe THF and ethanol were removed by rotary evaporation
  2. additiondiluted with 100 mL of water
  3. extractionextracted with ether (200 mL)
  4. customto remove any neutral impurities
  5. filtrationthe resulting white solids were collected by filtration
  6. washwashed with water and hexanes
  7. customAfter air-drying

出典と根拠

ORDレコード
ord-2c4849f46c174d14ae86d9630ef521cc
出典データセット
uspto-grants-2016_09
特許番号
US09447035B2

反応ノート

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