Lithium Hydroxide → HCID 118380493, compound

HRID 627058Notes

Reaction equation

HRID 627058 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:37])[C@@H:9]([CH3:36])[C:10]([NH:12][C@@H:13]([CH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)[C:14]([N:16]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH2:18][C@H:17]1[C:25]([O:27]CC)=[O:26])=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[Li+].[OH-].OS([O-])(=O)=O.[K+]>C(O)C>[C:1]([O:5][C:6]([N:8]([CH3:37])[C@@H:9]([CH3:36])[C:10]([NH:12][C@@H:13]([CH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)[C:14]([N:16]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH2:18][C@H:17]1[C:25]([OH:27])=[O:26])=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 516920Potassium bisulfateHCID 131735273(S)-ethyl 1-((S)-2-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Product 1

HCID 118380493HCID 118380493, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 mL round-bottomed flask, (S)-ethyl 1-((S)-2-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (188 mg, 363 μmol, Eq: 1.00) was combined with THF (3 mL) and ethanol (1 mL) to give a colorless solution. Aqueous 1 M LiOH (1.1 mL, 1.1 mmol, Eq: 3) was added and the reaction was stirred at rt for 1 h. Aqueous 0.1 M KHSO4 (10 mL) was added and the resulting mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give (S)-1-((S)-2-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (135 mg), m/z=491 (M+H).

Workup

  1. customto give a colorless solution
  2. extractionthe resulting mixture was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ede9d6c91ad447d802b8283e9b83a73
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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