Hydrochloric Acid → HCID 68767718, compound

HRID 1172330Notes

Reaction equation

HRID 1172330 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C:6]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17]CC)=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH2:4][C@H:3]1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27].O1CCCC1.O.[Li+].[OH-].Cl>CCOCC>[NH2:1][C@@H:2]1[CH2:7][C:6]([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH2:4][C@H:3]1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21881883Oxolane--water (1/1)HCID 68774314HCID 68774314, compound

Product 1

HCID 68767718HCID 68767718, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of Example 11C (36 mg, 0.088 mmol) in mixture of tetrahydrofuran/H2O (0.3 mL/0.15 mL), LiOH (23 mg, 0.53 mmol) was added at room temperature. The reaction mixture was stirred overnight. It was acidified with 2N HCl in ether until pH=3 and purified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid) to provide the title compound (25 mg, 75%). 1H NMR (500 MHz, DMSO-d6) δ ppm 7.90-8.07 (m, 3H), 7.67 (s, 1H), 7.47-7.58 (m, 2H), 6.01-6.14 (m, 1H), 3.66-3.96 (m, 2H), 2.57-3.04 (m, 4H), 1.65-2.46 (m, 9H). MS (ESI) m/z 383 (M+H)+.

Workup

  1. additionwas added at room temperature
  2. custompurified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-4e8a472979d84c7eaa5cada8ef029f64
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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