Hydrochloric Acid → HCID 68769938, compound

HRID 1172340Notes

Reaction equation

HRID 1172340 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C:6]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([O:17]CC)=[O:16])[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].[Li+].[OH-].Cl>O1CCCC1.O.CCOCC>[NH2:1][C@@H:2]1[CH2:7][C:6]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([OH:17])=[O:16])[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 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 131728424HCID 131728424, compound

Product 1

HCID 68769938HCID 68769938, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of Example 17B (55 mg, 0.13 mmol) in a mixture of tetrahydrofuran/H2O (1.0 mL/0.5 mL), LiOH (19 mg, 0.80 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 (32 mg, 63%). 1H NMR (400 MHz, methanol-d4) δ ppm 7.78 (s, 1H), 7.55-7.52 (m, 1H), 7.42-7.38 (m, 1H), 6.21 (s, 1H), 4.0-3.90 (m, 1H) 3.85-3.70 (m, 2H), 3.65-3.50 (m, 1H), 3.20-2.8 (m, 3H), 2.75-2.55 (m, 3H), 2.50-2.40 (m, 3H), 2.35-2.20 (m, 2H), 2.05-1.85 (m, 2H). MS (APCI) 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-af209da677fa43ca8257ea4270eafee6
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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