Lithium hydroxide, monohydrate → HCID 59700560, compound

HRID 901853Notes

Reaction equation

HRID 901853 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][CH2:12][CH2:13][NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C@H:22]([O:28][CH3:29])[C:23]([O:25]CC)=[O:24])=[CH:17][CH:16]=3)[CH2:9][CH2:8][O:7][C:6]=2[CH:30]=1.O.[OH-].[Li+]>CO.C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][CH2:12][CH2:13][NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C@H:22]([O:28][CH3:29])[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=3)[CH2:9][CH2:8][O:7][C:6]=2[CH:30]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10112606HCID 10112606, compound

Product 1

HCID 59700560HCID 59700560, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

(S)-Ethyl 3-[4-{3-(7-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazin-4-yl)propylamino}phenyl]-2-methoxypropanoate (1.0 g, 1 eq, 2.4 mmol) obtained in example 49, was hydrolyzed using lithium hydroxide monohydrate (151 mg, 1.5 eq, 3.6 mmol) in methanol-THF-water at RT till all the starting material is consumed (4 to 5 h). The reaction mixture was diluted with water, acidified (pH ˜4-5) with dil. HCl and then extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated on rotary evaporator. The residue was chromatographed using ethyl acetate and hexanes→methanol and chloroform to afford the title compound (650 mg, yield 70%) as viscous liquid.

Workup

  1. customat RT
  2. customis consumed (4 to 5 h)
  3. additionThe reaction mixture was diluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated on rotary evaporator
  7. customThe residue was chromatographed

Sources & evidence

ORD record
ord-a4ad20b4f7b84f8d94a0e7ffd8a403f8
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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