Hydrochloric Acid → HCID 67071684, compound

HRID 874275Notes

Reaction equation

HRID 874275 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:29])/[CH:6]=[CH:7]/[C:8]1[CH:9]=[C:10]2[C:25](=[CH:26][CH:27]=1)[O:24][C:13]1([CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]1)[CH2:12][C:11]2=[O:28].Cl>O.O1CCOCC1>[C:20]([O:19][C:17]([N:15]1[CH2:14][C:13]2([CH2:12][C:11](=[O:28])[C:10]3[C:25](=[CH:26][CH:27]=[C:8](/[CH:7]=[CH:6]/[C:5]([OH:29])=[O:4])[CH:9]=3)[O:24]2)[CH2:16]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67071422HCID 67071422, compound2×

Product 1

HCID 67071684HCID 67071684, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

1 M NaOH (1.60 ml) was added to a solution of (E)-3-[1′-tert-butoxycarbonyl-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl]-acrylic acid methyl ester (Intermediate 4, Step B, 450 mg, 1.20 mmol) in water (11 ml) and dioxane (22 ml). The mixture was stirred at RT for 5 h. Aqueous HCl 10% was added until reaching pH 7, dioxane was removed under vacuum and the residue was diluted with water. The aqueous layer was acidified to pH 5 with 10% aqueous HCl and the product was extracted with DCM (3×30 ml). The collected organic phases were dried over Na2SO4 and concentrated to give (E)-3-[1′-tert-butoxycarbonyl-4-oxo-spiro(chromane-2,3′-azetidine)-6-yl]-acrylic acid (430 mg) as a yellow solid.

Workup

  1. customwas removed under vacuum
  2. additionthe residue was diluted with water
  3. extractionthe product was extracted with DCM (3×30 ml)
  4. dry with materialThe collected organic phases were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-783356531bdf49db94a15206c70bcc63
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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