Hydrochloric Acid → HCID 59515686, compound

HRID 1161257Notes

Reaction equation

HRID 1161257 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:29])[C:9]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH:14]=[CH:15][N:16]([C@H:23]([CH3:28])[C:24]([O:26]C)=[O:25])[C:17]3=[O:22])=[O:10])=[CH:4][CH:3]=1.[OH-].[Li+].C(O)(C)(C)C.O.Cl>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:29])[C:9]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH:14]=[CH:15][N:16]([C@H:23]([CH3:28])[C:24]([OH:26])=[O:25])[C:17]3=[O:22])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 6386tert-ButanolHCID 59515658HCID 59515658, compound

Product 1

HCID 59515686HCID 59515686, compound

Procedure

(R)-Methyl 2-(5-((S)-2-(4-chlorophenyl)propanamido)-1-oxoisoquinolin-2(1H)-yl)propanoate (0.23 g, 0.00050 mol) was stirred with lithium hydroxide (0.03 g, 0.001 mol) in tert-butyl alcohol (4 mL, 0.04 mol) and water (2 mL, 0.1 mol) at 0° C. for 1 hour. 1 N HCl was added until pH<7 and the reaction mixture was extracted with CH2Cl2 (40 mL×3). The organic layers were dried over MgSO4, filtered, purified via flash chromatography (12 g of silica gel, 0-50% EtOAc/Hexane) and gave a light yellow solid. 1H NMR δ (CDCl3) δ: 8.05-8.01 (m, 1H), 7.89-7.62 (m, 2H), 7.38-7.29 (m, 5H), 6.89-6.80 (m, 1H), 6.04-5.94 (m, 1H), 5348-5.39 (m, 1H), 3.86 (d, J=6.6 Hz, 1H), 3.03-2.88 (m, 6H). MS m/z 399.0 (M+H)+.

Workup

  1. extractionthe reaction mixture was extracted with CH2Cl2 (40 mL×3)
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltered
  4. custompurified via flash chromatography (12 g of silica gel, 0-50% EtOAc/Hexane)
  5. customgave a light yellow solid

Sources & evidence

ORD record
ord-eb6217ebd25b4e018429d220067cdd8e
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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