Water → 3-(Benzyloxy)-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylic acid

HRID 1365743Notes

Reaction equation

HRID 1365743 reaction equation
[CH2:1]([O:8][C:9]1[C:21](=[O:22])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][C:18]([CH3:20])([CH3:19])[C:12]2=[N:11][C:10]=1[C:23]([O:25]CC)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].O>C1COCC1>[CH2:1]([O:8][C:9]1[C:21](=[O:22])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][C:18]([CH3:20])([CH3:19])[C:12]2=[N:11][C:10]=1[C:23]([OH:25])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58877852Ethyl 3-(benzyloxy)-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylate

Product 1

HCID 588778933-(Benzyloxy)-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylic acidYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(benzyloxy)-10,10-dimethyl-4-oxo-6,7,9,10-tetrahydro-4H-pyrimido[1,2-d][1,4]oxazepine-2-carboxylate (920 mg, 2.5 mmol) was dissolved in 5 mL of THF and to it was added with stirring LiOH (120 mg, 5 mmol) and 5 mL water. After 30 min, the THF was evaporated and the aqueous layer was acidified with dil HCl. This was extracted with CH2Cl2, dried (MgSO4), filtered and concentrated. Trituration from Et2O gave the title compound (790 mg, 91%) as a solid: 1H NMR (300 MHz, CDCl3) δ: 1.40 (s, 6H), 3.60 (s, 2H), 3.65-3.95 (m, 2H), 4.10-4.90 (m, 2H), 5.41 (s, 2H), 7.25-7.42 (m, 3H), 7.45-7.58 (m, 2H). LC/MS (M+H): 345.

Workup

  1. customthe THF was evaporated
  2. extractionThis was extracted with CH2Cl2
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-23ac3ebecc414ddf801866527fd2dd2b
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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