Hydrochloric Acid → HCID 58188124, compound

HRID 1845153Notes

Reaction equation

HRID 1845153 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:8]=[C:9]([C:11](=[O:17])[NH:12][C@@H:13]([CH3:16])[CH2:14][OH:15])[CH:10]=1)=[O:4].[OH-].[Li+].C1COCC1.Cl>O>[OH:15][CH2:14][C@@H:13]([NH:12][C:11]([C:9]1[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:8]=1)=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58188282HCID 58188282, compound

Product 1

HCID 58188124HCID 58188124, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of (S)-methyl5-(1-hydroxypropan-2-ylcarbamoyl)-4′-methylbiphenyl-3-carboxylate (105 mg, 0.321 mmol), lithium hydroxide (9.98 mg, 0.417 mmol), THF (3 mL), and water (1 mL) was stirred at room temperature for 12 h. LC-MS indicated completion of the reaction. The reaction mixture was diluted with water (5 mL) and acidified with 1N aq. HCl to pH=3 and extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to yield a white solid. LC-MS: 314.4 [M+1]+.

Workup

  1. customcompletion of the reaction
  2. extractionextracted with EtOAc (50 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto yield a white solid

Sources & evidence

ORD record
ord-57b08c11869e4138ad5be48af3d47b67
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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