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Phosgene → 1-{[1-[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 1822433
ノート
印刷プレビュー

反応式

HRID 1822433 の反応式
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][NH:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].[C:38]([O-:41])(O)=O.[Na+].C(Cl)(Cl)=O.[NH2:47][CH:48]([C:62]([CH3:65])([CH3:64])[CH3:63])[C:49]([NH:51][CH:52]1[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH2:54][CH:53]1[OH:61])=[O:50]>C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:21]=3)[CH2:16][N:15]2[C:38](=[O:41])[NH:47][CH:48]([C:49](=[O:50])[NH:51][CH:52]2[C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)[CH2:54][CH:53]2[OH:61])[C:62]([CH3:65])([CH3:63])[CH3:64])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6371PhosgeneHCID 516892Sodium Bicarbonate2 回HCID 207653161-{[4-(7-Methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl esterHCID 68488353HCID 68488353、化合物

生成物 1

HCID 68491628
1-{[1-[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of compound 12 (0.13 mmol) in THF (2 mL), was added a large excess of NaHCO3 (s) and a solution of phosgene in toluene (1.6 M, 600 μL). After 10 min of agitation the slurry was filtered and concentrated to dryness. The solid was redissolved in dichloromethane and a large excess of NaHCO3 (s) and 2-Amino-N-(2-hydroxy-indan-1-yl)-3,3-dimethyl-butyramide (0.65 mmol) was added. The slurry was agitated for 24-40 hrs at RT. The slurry was filtered, concentrated and subjected to silica column chromatography (gradient elution from 100% DCM to MeOH/DCM 2:98) to give the title compound (89.6 mg, 0.11 mmol). Purity by HPLC>95%. M+H+790.3.

後処理

  1. filtrationAfter 10 min of agitation the slurry was filtered
  2. concentrationconcentrated to dryness
  3. dissolutionThe solid was redissolved in dichloromethane
  4. filtrationThe slurry was filtered
  5. concentrationconcentrated
  6. washsubjected to silica column chromatography (gradient elution from 100% DCM to MeOH/DCM 2:98)

出典と根拠

ORDレコード
ord-d21af08ca24347b9adb361426472cc9e
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07608590B2

反応ノート

読み込み中…

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