Hydrochloric Acid → HCID 69189469, compound

HRID 560173Notes

Reaction equation

HRID 560173 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[C:5]2[CH2:14][CH2:15][CH2:16][NH:17]C(OC(C)(C)C)=O.[ClH:25].C(OCC)C>C(Cl)Cl.O1CCOCC1>[ClH:25].[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[C:5]2[CH2:14][CH2:15][CH2:16][NH2:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 58172097HCID 58172097, compound

Product 1

HCID 69189469HCID 69189469, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To 5-bromo-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid (55 mg, 0.14 mmol, 1.0 equiv) in methylene chloride (5 mL) at 0° C. was added 0.2 mL of 4M HCl in dioxane. The reaction was stirred at ambient temperature for 1 h. Then 10 mL of diethyl ether was added to the reaction and the reaction concentrated. To this residue was added 10 mL diethyl ether and the solid was filtered off and washed with diethyl ether several times and air dried for 15 min to provide the title compound (32 mg); MS, electrospray, 298 (M+H).

Workup

  1. concentrationthe reaction concentrated
  2. additionTo this residue was added 10 mL diethyl ether
  3. filtrationthe solid was filtered off
  4. washwashed with diethyl ether several times and air
  5. customdried for 15 min

Sources & evidence

ORD record
ord-1cf3a7ad85644a91979f4b696d598f94
Source dataset
uspto-grants-2011_11
Patent number
US08063094B2

Reaction notes

Loading…