Lithium hydroxide, monohydrate → HCID 59845662, compound

HRID 1819456Notes

Reaction equation

HRID 1819456 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][NH:5][C:6]1[N:11]=[C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:15]2)[C:9]([N+:28]([O-:30])=[O:29])=[CH:8][N:7]=1.O.[OH-].[Li+]>CO.O>[C:24]([O:23][C:21]([NH:20][CH:17]1[CH2:18][CH2:19][CH:14]([CH2:13][NH:12][C:10]2[C:9]([N+:28]([O-:30])=[O:29])=[CH:8][N:7]=[C:6]([NH:5][CH2:4][C:3]([OH:31])=[O:2])[N:11]=2)[CH2:15][CH2:16]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59845668HCID 59845668, compound

Product 1

HCID 59845662HCID 59845662, compoundYield 124%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of {4-[(4-tert-butoxycarbonylamino-cyclohexylmethyl)-amino]-5-nitro-pyrimidin-2-ylamino}-acetic acid methyl ester (845 mg, 1.9 mmol) in a mixture of MeOH (90 mL) and water (30 mL) was added lithium hydroxide monohydrate (404 mg, 9.6 mmol). The heterogeneous mixture was stirred at room temperature for 1 h. The mixture was concentrated and the resulting residue was acidified to pH 5 using 1M HCl. The product was extracted using ethyl acetate (×3). The combined organic phase was dried over Na2SO4 and concentrated to yield 1.0 g of the crude {4-[(4-tert-butoxycarbonylamino-cyclohexylmethyl)-amino]-5-nitro-pyrimidin-2-ylamino}-acetic acid as a white solid. This product was used for the next reaction without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionThe product was extracted
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4cafc60ce1e64cf79c4119fdfa91a81a
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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