Lithium hydroxide, monohydrate → HCID 117690842, compound

HRID 58815Notes

Reaction equation

HRID 58815 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:16][C@H:17]([NH:22][C:23](=[O:36])[C@@H:24]([NH:26][C:27](=[O:35])[CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH3:25])[C:18]([O:20]C)=[O:19])[CH:12]=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].O>O.C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:16][C@H:17]([NH:22][C:23](=[O:36])[C@@H:24]([NH:26][C:27](=[O:35])[CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH3:25])[C:18]([OH:20])=[O:19])[CH:12]=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 130384719HCID 130384719, compound

Product 1

HCID 117690842HCID 117690842, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

(S)-Methyl 3-(3-(benzyloxy)-4-methylphenyl)-2-((S)-2-(2-morpholinoacetamido) propanamido)propanoate (1.2 g, 2.4 mmol) was treated with a solution of lithium hydroxide-H2O (300 mg, 7.2 mmol) in water/THF (10 mL/10 mL) for 30 min. The THF was removed and the aqueous phase was acidified to pH=3-4 with 1 N HCl and then concentrated to dryness to afford (S)-3-(3-(benzyloxy)-4-methylphenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanoic acid, which was used directly without further purification.

Workup

  1. customThe THF was removed
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-145f441dbfcf49b0a5a6faca991e2d72
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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