Hydrochloric Acid → Fmoc-3-amino-4'-carboxybiphenyl

HRID 1976811노트

반응식

HRID 1976811 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=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.O1CCOCC1>[C:23]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 27563554-(3-aminophenyl)benzoic Acid

생성물 1

HCID 2756228Fmoc-3-amino-4'-carboxybiphenyl

시약·촉매·용매 2

HCID 312751,4-Dioxane용매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
3 °C

실험 절차

Dissolve 3′-aminobiphenyl-4-carboxylic acid (Preparation B, Step 3) (1.07 g, 5 mmol) and Na2CO3 (1.33 g, 12.5 mmol ) in H2O-dioxane (2:1, 45 mL), and cool the solution to ˜3° C. Add Fmoc-Cl (1.3 g) in dioxane (10 ml); stir at ice bath temperature for 3 hours, allow to warm to room temperature and stir for another 4 hours. Pour into ice water and acidify with aqueous HCl. Extract with EtOAc. Dry extracts over MgSO4, and strip solvent in vacuo. Recrystallize residue from CH3CN to give the title compound. HPLC Retention Time, 22.6 minutes (condition (b)).

후처리

  1. temperatureto warm to room temperature
  2. stirringstir for another 4 hours
  3. extractionExtract with EtOAc
  4. customDry

출처 및 근거

ORD 기록
ord-46a78b4ac1bb4a96a85ab1de651bf071
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06228985B1

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