Lithium hydroxide, monohydrate → HCID 57988391, compound

HRID 2081120Notes

Reaction equation

HRID 2081120 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=1)[O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][N:11]([C:16](=[O:30])[C@@H:17]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:10]([C:31]([NH:33][C@:34]1([C:39]([O:41]CC)=[O:40])[CH2:36][C@H:35]1[CH:37]=[CH2:38])=[O:32])[CH2:9]2.O.[OH-].[Li+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=1)[O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][N:11]([C:16](=[O:30])[C@@H:17]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:10]([C:31]([NH:33][C@:34]1([C:39]([OH:41])=[O:40])[CH2:36][C@H:35]1[CH:37]=[CH2:38])=[O:32])[CH2:9]2

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57988353HCID 57988353, compound

Product 1

HCID 57988391HCID 57988391, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The crude (1R,2S)-ethyl 1-(6-(3-chlorophenoxy)-2-((S)-2-(4-fluorophenylamino)-3,3-dimethylbutanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)-2-vinylcyclopropanecarboxylate (130 mg, 0.20 mmol) was dissolved in 1.0 mL of a mixture of THF:MeOH:H2O (2:1:1). Lithium hydroxide monohydrate (0.050 g, 1.2 mmol) was added and reaction stirred at rt overnight. The reaction was then concentrated under vacuum and quenched with 5 mL of 1 N HCl. The product precipitated and could be filtered off giving an off-white powder (110 mg). It was directly used in the next step without further purification. MS m/e 619 (M−−H).

Workup

  1. customreaction
  2. concentrationThe reaction was then concentrated under vacuum
  3. customquenched with 5 mL of 1 N HCl
  4. customThe product precipitated
  5. filtrationcould be filtered off

Sources & evidence

ORD record
ord-02e6f5f5d347433499cbb063f8500e54
Source dataset
uspto-grants-2011_04
Patent number
US07932277B2

Reaction notes

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