HCID 57989046, compound → HCID 57989136, compound

HRID 471055Notes

Reaction equation

HRID 471055 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:30]=[CH:31][CH:32]=1)[CH2:10][N:11]1[CH2:29][CH2:28][C:14]2([O:19][CH2:18][CH2:17][N:16]([C:20]([C:22]3[S:23][C:24]([CH3:27])=[CH:25][CH:26]=3)=[O:21])[CH2:15]2)[CH2:13][CH2:12]1)C>C(O)(=O)C.O>[CH3:27][C:24]1[S:23][C:22]([C:20]([N:16]2[CH2:15][C:14]3([CH2:13][CH2:12][N:11]([CH2:10][C:9]4[CH:8]=[C:7]([CH:32]=[CH:31][CH:30]=4)[O:6][CH2:5][CH:4]=[O:3])[CH2:29][CH2:28]3)[O:19][CH2:18][CH2:17]2)=[O:21])=[CH:26][CH:25]=1

Participants

4

Reactant 1

HCID 57989046HCID 57989046, compound

Product 1

HCID 57989136HCID 57989136, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of (9-(3-(2,2-diethoxyethoxy)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone (example 38, step b) (0.45 g) in a mixture of acetic acid (25 mL) and water (25 mL) was heated at 65° C. under nitrogen for 16 hours. Most of the solvents were removed under reduced pressure and the residue partitioned between ethyl acetate and excess saturated sodium bicarbonate solution. The organic layer was dried over sodium sulphate and filtered, acetic acid (0.051 mL) was added and the solvent removed under reduced pressure to afford the subtitled compound. Yield 0.38 g. Used directly.

Workup

  1. customMost of the solvents were removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and excess saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. additionacetic acid (0.051 mL) was added
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bf035ad3a1c24713adbfdeae3ba123de
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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