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Triethylamine → HCID 178453994、化合物

HRID 2089039
ノート
印刷プレビュー

反応式

HRID 2089039 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([O:32]C)[CH:30]=3)[N:25]([S:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:24]=2)[CH:3]=1.B(Br)(Br)Br.C(N(CC)CC)C.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>C(Cl)Cl.[Cl-].[Na+].O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)[CH:5]=[C:4]([C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([OH:32])[CH:30]=3)[N:25]([S:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:24]=2)[CH:3]=1
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 8471TriethylamineHCID 25134Boron tribromideHCID 90495Di-tert-butyl dicarbonateHCID 178493666HCID 178493666、化合物

生成物 1

HCID 178453994HCID 178453994、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回
HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of Example 213d (0.927 g, 1.514 mmol) in CH2Cl2 (50 mL) was added 1M BBr3 in CH2Cl2 (10.6 mL, 10.6 mmol) at −78° C. The reaction was slowly warmed to room temperature and stirred overnight. The solvent was evaporated. To a suspension of the residue in THF (60.0 mL) was added triethylamine (1.48 mL, 10.6 mmol) and Boc2O (0.380 g, 1.74 mmol). The reaction was stirred for 8 hours, diluted with 50% brine, and extracted with EtOAc. The organic layers was dried over MgSO4, filtered, concentrated, and purified on a 40 g column using the ISCO Companion flash system eluting with CH2Cl2/EtOAc to give the title compound.

後処理

  1. customThe solvent was evaporated
  2. additionTo a suspension of the residue in THF (60.0 mL)
  3. stirringThe reaction was stirred for 8 hours
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layers was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on a 40 g column
  9. washeluting with CH2Cl2/EtOAc

出典と根拠

ORDレコード
ord-00db2ef7639e48c3ba9385bacea64c2a
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08435980B2

反応ノート

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