Hydrochloric Acid → HCID 71087561, compound

HRID 632460Notes

Reaction equation

HRID 632460 reaction equation
C[O:2][C:3](=[O:26])[C@@H:4]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:20][CH2:19]2)=[C:14]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[N:13]=1)=[O:11])[CH2:5][CH:6]1[CH2:8][CH2:7]1.O.O.[OH-].[Li+].Cl>C1COCC1>[CH:6]1([CH2:5][C@H:4]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:20][CH2:19]3)=[C:14]([O:21][CH2:22][CH:23]3[CH2:25][CH2:24]3)[N:13]=2)=[O:11])[C:3]([OH:26])=[O:2])[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 71087544HCID 71087544, compound

Product 1

HCID 71087561HCID 71087561, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-3-Cyclopropyl-2-[(5-cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carbonyl)-amino]-propionic acid methyl ester (Example 258, 42 mg, 117 μmol) was dissolved in THF (2 mL). After addition of water (0.66 mL) and lithium hydroxide monohydrate (14.8 mg, 352 μmol) the mixture was heated and stirred for 3 hours at reflux temperature. The mixture was cooled to room temperature, water (7 mL) was added and the mixture was acidified with 1 N HCl. The mixture was then extracted with ethyl acetate (14 and 7 mL), organic layers were washed with brine (10 mL), combined, dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound (36 mg, quant) as white solid; LC-MS (UV peak area/ESI) 100%, 345.1814 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature
  3. extractionThe mixture was then extracted with ethyl acetate (14 and 7 mL), organic layers
  4. washwere washed with brine (10 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2141b9d787994d5f96df8dc177060856
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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