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tert-Butyl bromoacetate → (6R,8S)-[3-(allyl-benzyloxycarbonyl-amino)-8-methyl-4-oxo-6-phenylcarbamoyl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl]-acetic acid tert-butyl ester

HRID 11001
ノート
印刷プレビュー

反応式

HRID 11001 の反応式
[CH2:1]([O:8][C:9](=[O:34])[N:10]([CH2:31][CH:32]=[CH2:33])[C:11]1[C:16](=[O:17])[N:15]2[C@H:18]([C:22](=[O:30])[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH:20]([CH3:21])[C:14]2=[N:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Br[CH2:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48]>C1COCC1>[C:50]([O:49][C:47](=[O:48])[CH2:46][C@@:20]1([CH3:21])[C:14]2=[N:13][CH:12]=[C:11]([N:10]([CH2:31][CH:32]=[CH2:33])[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:34])[C:16](=[O:17])[N:15]2[C@@H:18]([C:22](=[O:30])[NH:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:19]1)([CH3:53])([CH3:52])[CH3:51]
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

5

反応物 3

HCID 79177tert-Butyl bromoacetateHCID 2733832Lithium hexamethyldisilazaneHCID 69600916(6S,8RS)-allyl-(8-methyl-4-oxo-6-phenylcarbamoyl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-3-yl)-carbamic Acid Benzyl Ester

生成物 1

HCID 69600880(6R,8S)-[3-(allyl-benzyloxycarbonyl-amino)-8-methyl-4-oxo-6-phenylcarbamoyl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl]-acetic acid tert-butyl ester収率 59%

試薬・触媒・溶媒

1
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To Intermediate 18c (495.7 mg, 1.08 mmol) in THF at −78° C. was added LiHMDS (2.268 mL, 2.268 mmol) dropwise. After 10 min, tert-butyl bromoacetate was added and the mixture was stirred at −78° C. for 20 min. It was allowed to warm to −40° C. over 20 min, then quenched with NH4Cl. The reaction mixture was diluted with EtOAc, then washed with H2O, brine, dried (Na2SO4) and concentrated. It was purified by SiO2 chromatography (50% EtOAc/hexanes) to afford 367.9 mg (59%) of intermediate 38a.

後処理

  1. temperatureto warm to −40° C. over 20 min
  2. customquenched with NH4Cl
  3. additionThe reaction mixture was diluted with EtOAc
  4. washwashed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customIt was purified by SiO2 chromatography (50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-d64943344df842839afee007706c4b16
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07094783B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート