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

HRID 1976812Notes

Reaction equation

HRID 1976812 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 219992504′-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino][1,1′-biphenyl]-3-carboxylic acid

Reagents, catalysts & solvents 1

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

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-7cc9e2da4e4b4f2f897ba22abb26b8f4
Source dataset
uspto-grants-2001_05
Patent number
US06228985B1

Reaction notes

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