Sodium Hydroxide → HCID 52939429, compound

HRID 1400147Notes

Reaction equation

HRID 1400147 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:23]([CH2:29][CH2:30][CH:31]([F:33])[F:32])[C:24]([O:26]CC)=[O:25])[CH:8]=2)[N:3]=1.[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:23]([CH2:29][CH2:30][CH:31]([F:33])[F:32])[C:24]([OH:26])=[O:25])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67154029HCID 67154029, compound

Product 1

HCID 52939429HCID 52939429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1.2 g of ethyl 2-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-5,5-difluoropentanoate are dissolved in 15 ml of tetrahydrofuran, and 10 ml of 2N sodium hydroxide solution are added. The mixture is stirred at 50° C. for 4 h and subsequently evaporated in vacuo. The mixture is then adjusted to pH2 using 25% hydrochloric acid with ice-cooling, with yellow crystals precipitating. The precipitate obtained is filtered off and dried in vacuo. Yield: 800 mg (71%) of 2-[2-amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-5,5-difluoropentanoic acid; LC-MS retention time: 1.35 min (“nonpolar” gradient).

Workup

  1. customsubsequently evaporated in vacuo
  2. temperaturecooling, with yellow crystals
  3. customprecipitating
  4. customThe precipitate obtained
  5. filtrationis filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9c57ea45ade1419a9e8d24c38707cca0
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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