Lithium Hydroxide → HCID 118380531, compound

HRID 627018Notes

Reaction equation

HRID 627018 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[C:10]([N:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH2:14][CH:13]1[C:21]([O:23]C)=[O:22])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Li+]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[C:10]([N:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[CH2:14][CH:13]1[C:21]([OH:23])=[O:22])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 118380523HCID 118380523, compound

Product 1

HCID 118380531HCID 118380531, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 50 mL round-bottomed flask, methyl 1-((S)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (660 mg, 1.58 mmol, Eq: 1.00) was combined with THF (14.8 mL) and methanol (4.95 mL) to give a colorless solution. The solution was cooled in an ice-bath and 1 M aqueous lithium hydroxide (4.74 mL, 4.74 mmol, Eq: 3) was added. The cooling bath was removed and the reaction was stirred at rt for 1 h. 0.1 M Aqueous KHSO4 (4 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 1-((S)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid as a white solid (600 mg), m/z=404 (M+H).

Workup

  1. customto give a colorless solution
  2. temperatureThe solution was cooled in an ice-bath
  3. customThe cooling bath was removed
  4. addition0.1 M Aqueous KHSO4 (4 mL) was added
  5. extractionthe resulting mixture was extracted with EtOAc
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c38762a5692e45eab3a3ed4da6fa800f
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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