Hydrochloric Acid → (2R,4S)-1-(tert-Butoxycarbonyl)-4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-2-carboxylic acid

HRID 2189211Notes

Reaction equation

HRID 2189211 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:18]=[C:17]([NH:19][C@@H:20]2[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@@H:22]([C:32]([O:34]C)=[O:33])[CH2:21]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.O.[OH-].[Li+].O1CCOCC1.Cl>O>[C:28]([O:27][C:25]([N:23]1[CH2:24][C@@H:20]([NH:19][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[N:18]=2)[CH2:21][C@@H:22]1[C:32]([OH:34])=[O:33])=[O:26])([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 67365675(2R,4S)-1-tert-butyl 2-methyl 4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 67366705(2R,4S)-1-(tert-Butoxycarbonyl)-4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-2-carboxylic acidYield 96.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(2R,4S)-1-tert-Butyl 2-methyl 4-(2-(2-methoxyphenyl)quinazolin-4-ylamino)pyrrolidine-1,2-dicarboxylate (0.415 g, 0.851 mmol) and lithium hydroxide monohydrate (0.089 g, 2.128 mmol) were dissolved in water (8 mL) and dioxane (8 mL) and stirred for 1 hour. Water (30 mL) was added and the mixture was acidified to pH 4 with 1M HCl. The aqueous layer was extracted with ethyl acetate (4×30 mL). The combined organic extracts were dried (MgSO4) and concentrated to give the title compound as a solid (0.382 g, 95%).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (4×30 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0f0c6f13633c4952ad11d54765294b14
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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