Hydrochloric Acid → HCID 89544628, compound

HRID 2283405Notes

Reaction equation

HRID 2283405 reaction equation
C([O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:33])[C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([C@H:21]([NH:24]C(OC(C)(C)C)=O)[CH2:22][CH3:23])[C:15]=2[F:32])[CH:8]=1)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[NH2:24][C@@H:21]([C:16]1[C:15]([F:32])=[C:14]([C:19]([Cl:20])=[CH:18][CH:17]=1)[C:13]([C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:6]([OH:34])=[O:5])=[O:33])[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89545058HCID 89545058, compound

Product 1

HCID 89544628HCID 89544628, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 2 To a solution of 3-[3-((R)-1-tert-Butoxycarbonylamino-propyl)-6-chloro-2-fluoro-benzoyl]-benzoic acid tert-butyl ester (219 mg, 0.45 mmol) in DCM (5 mL) was added 4M HCl in dioxane (0.445 mL, 1.78 mmol, 4 eq) and the reaction stirred for 18 h. Complete conversion. Mixture was concentrated and then triturated with diethyl ether (˜1 mL) and the solid filtered off to give 3-[3-((R)-1-amino-propyl)-6-chloro-2-fluoro-benzoyl]-benzoic acid (154 mg, 0.41 mmol, 92%). [M+H]+ 336

Workup

  1. concentrationMixture was concentrated
  2. customtriturated with diethyl ether (˜1 mL)
  3. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-c68d78f4c2a544219bde42896ff7f322
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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