Hydrochloric Acid → HCID 70229029, compound

HRID 1976813Notes

Reaction equation

HRID 1976813 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1.C([O-])([O-])=O.[Na+].[Na+].[C:24](Cl)([O:26][CH2:27][CH:28]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25].Cl>O.O1CCOCC1.CCOC(C)=O>[C:24]([CH:2]([NH2:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1)([O:26][CH2:27][CH:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:35]2[C:40]1=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 21999247HCID 21999247, compound

Product 1

HCID 70229029HCID 70229029, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
5 °C

Procedure

Cool to 5° C. a mixture of 2′-aminomethylbiphenyl-4-carboxylic acid (Preparation D, Step 5) (1.14 g, 5.0 mmol) and Na2CO3 (1.33 g, 12.5 mmol) in water:dioxane (2:1, 70 mL). Add Fmoc-Cl (1.3 g, 5.0 mmol) and stir at ice-bath temperature for 4 hours, then overnight at room temperature. Pour into a mixture of warm EtOAc (1 L) and 1N aqueous HCl (100 mL) and stir vigorously. Separate organic layer, dry (MgSO4), and concentrate in vacuo until solids appear. Collect the title compound, m.p. 215-218° C. MS (Cl+/CH4) m/z 450 [M+H]+.

Workup

  1. customovernight
  2. customat room temperature
  3. dry with materialSeparate organic layer, dry (MgSO4)
  4. concentrationconcentrate in vacuo until solids
  5. customCollect the title compound, m.p. 215-218° C

Sources & evidence

ORD record
ord-250a1dfcdfb44dd78652996401b4b1ec
Source dataset
uspto-grants-2001_05
Patent number
US06228985B1

Reaction notes

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