Hydrochloric Acid → 4'-((((9H-Fluoren-9-YL)methoxy)carbonyl)amino)-[1,1'-biphenyl]-3-carboxylic acid

HRID 1976812ノート

反応式

HRID 1976812 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:23](Cl)([O:25][CH2:26][CH:27]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24].Cl>O.O1CCOCC1>[C:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=2)=[CH:6][CH:7]=1)([O:25][CH2:26][CH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]2[C:39]1=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:24]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 27723004'-aminobiphenyl-3-carboxylic acid

生成物 1

HCID 219992504'-((((9H-Fluoren-9-YL)methoxy)carbonyl)amino)-[1,1'-biphenyl]-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

Cool a mixture of 4′-aminobiphenyl-3-carboxylic acid (Preparation C, Step 4) (7.46 g, (35 mmol) and Na2CO3 (9.3 g, 87.7 mmol) in H2O /dioxane (2:1, 300 mL) to ˜5° C. Add Fmoc-Cl (9.05 g, 35 mmol), and stir the mixture at ice bath temperature for 4 hours. Allow reaction mixture to warm to room temperature and stir for 24 hours. Pour into ice water, and acidify with aqueous HCl. Collect the precipitate, wash with water, and dry in vacuo. Recrystallize from EtOAc to give the title compound, m.p. 270.5-272° C. HPLC; FAB MS m/z 436 [M+H]+.

後処理

  1. temperatureCool
  2. customAllow reaction mixture
  3. customCollect the precipitate
  4. washwash with water
  5. customdry in vacuo
  6. customRecrystallize from EtOAc

出典と根拠

ORDレコード
ord-7cc9e2da4e4b4f2f897ba22abb26b8f4
出典データセット
uspto-grants-2001_05
特許番号
US06228985B1

反応ノート

読み込み中…