Hydrochloric Acid → HCID 66813374, compound

HRID 1944775Notes

Reaction equation

HRID 1944775 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-57bf040617644b39b45dfb3393842f6f
Source dataset
uspto-grants-2013_03
Patent number
US08394846B2

Reaction notes

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