Lithium Hydroxide → HCID 10460204, compound

HRID 2113615Notes

Reaction equation

HRID 2113615 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[CH2:10][C:11]1[N:20]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=2)[C:18]2[C:13](=[CH:14][C:15]([C:32]3[C:37]([C:38]([F:41])([F:40])[F:39])=[CH:36][CH:35]=[CH:34][N:33]=3)=[CH:16][CH:17]=2)[N:12]=1)=[O:4].[Li+].[OH-]>C1COCC1.O>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:19]2[C:18]3[C:13](=[CH:14][C:15]([C:32]4[C:37]([C:38]([F:40])([F:41])[F:39])=[CH:36][CH:35]=[CH:34][N:33]=4)=[CH:16][CH:17]=3)[N:12]=[C:11]([CH2:10][N:6]3[CH2:7][CH2:8][CH2:9][C@H:5]3[C:3]([OH:4])=[O:2])[N:20]=2)=[CH:27][CH:26]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58628192HCID 58628192, compound

Product 1

HCID 10460204HCID 10460204, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of (S)-1-[4-(4-tert-butyl-phenylamino)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-ylmethyl]-pyrrolidine-2-carboxylic acid methyl ester (140 mg, 0.248 mmol) in THF (20 ml) and H2O (20 ml), add LiOH (18 mg, 0.745 mmol). Stir the mixture for 2 hours at 50° C. Concentrate, add water, extract with ether, acidify the aqueous layer to pH 6-7, extract with EtOAc, and concentrate to give (S)-1-[4-(4-tert-butyl-phenylamino)-7-(3-trifluoromethyl-pyridin-2-yl)-quinazolin-2-ylmethyl]-pyrrolidine-2-carboxylic acid.

Workup

  1. concentrationConcentrate
  2. additionadd water
  3. extractionextract with ether
  4. extractionextract with EtOAc
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-5d6b2d19c04f4ab4ac75e47c49945969
Source dataset
uspto-grants-2008_10
Patent number
US07432275B2

Reaction notes

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