Hydrochloric Acid → HCID 71737378, compound

HRID 1481081Notes

Reaction equation

HRID 1481081 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21]([NH:23][C@H:24]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@H:25]([OH:30])[C:26]([O:28]C)=[O:27])=[O:22])[N:4]=1)#[N:2].O.CCOC(C)=O.Cl>CO.[OH-].[Na+]>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21]([NH:23][C@H:24]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@H:25]([OH:30])[C:26]([OH:28])=[O:27])=[O:22])[N:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 89812930HCID 89812930, compound

Product 1

HCID 71737378HCID 71737378, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

(2S,3R)-Methyl 3-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)-2-hydroxy-4-phenylbutanoate (4 mg, 0.01 mmol) was dissolved in MeOH (2 mL) and 2 N NaOH (2 mL). After stirring for 6 hours at room temperature, H2O (15 mL) and EtOAc (15 mL) were added. To the stirred mixture was added 1 N hydrochloric acid until pH was 1. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-30% MeOH/CH2Cl2) to give the title compound in 3 mg. MS: (−) m/z 482.30 (M−1).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted twice with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography (0-30% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1091a1df851c487fb760e2b2cc5fa768
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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