Hydrochloric Acid → HCID 66813374, compound

HRID 504257Notes

Reaction equation

HRID 504257 reaction equation
C([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]([CH2:28][CH2:29][NH:30]C(OC(C)(C)C)=O)[C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])(C)(C)C.Cl>O1CCOCC1>[NH2:30][CH2:29][CH2:28][N:21]([CH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:9]2[C:8]([C:6]([OH:7])=[O:5])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:19][CH:18]=1)[C:22](=[O:27])[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66813774HCID 66813774, compound

Product 1

HCID 66813374HCID 66813374, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4′-[(2-t-Butoxycarbonylaminoethyl)pentanoylamino]methylbiphenyl-2-carboxylic acid t-butyl ester (3b) and 4′-[(2-aminoethyl)pentanoylamino]methylbiphenyl-2-carboxylic acid (3c): Valeryl chloride (4.6 mL, 38.7 mmol) was added to a solution of crude intermediate (3a) (15 g, 35.2 mmol) in toluene (100 mL) at 0° C. followed by the addition of DIPEA (18.4 mL, 105 mmol). The mixture was stirred at room temperature for 3 hours. 1M aqueous NaOH (10 mL) was added and the mixture was concentrated in vacuo. The concentrate was extracted with EtOAc (3×150 mL) and water (80 mL). The organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to afford crude intermediate (3b). A solution of crude intermediate (3b), 1,4-dioxane (50 mL) and 4M HCl in 1,4-dioxane (50 mL) was stirred for 40 minutes at room temperature. The precipitate was filtered and purified by reverse phase HPLC to afford intermediate (3c).

Workup

  1. filtrationThe precipitate was filtered
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-5859a3b692e843be8107e2364b8d1fc1
Source dataset
uspto-grants-2010_08
Patent number
US07777077B2

Reaction notes

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