Lithium Hydroxide → HCID 58550886, compound

HRID 1907979Notes

Reaction equation

HRID 1907979 reaction equation
[N:1]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:6][CH2:5][C:4]2([O:11][C:10]3[CH:12]=[C:13]([C:16]([O:18]C)=[O:17])[CH:14]=[CH:15][C:9]=3[N:8]3[CH:20]=[CH:21][CH:22]=[C:7]23)[CH2:3][CH2:2]1.[Li+].[OH-]>O1CCOCC1.C(OCC)(=O)C>[C:26]([O:25][C:23]([N:1]1[CH2:2][CH2:3][C:4]2([O:11][C:10]3[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=[CH:15][C:9]=3[N:8]3[CH:20]=[CH:21][CH:22]=[C:7]23)[CH2:5][CH2:6]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58551585HCID 58551585, compound

Product 1

HCID 58550886HCID 58550886, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1′-tert-butyl 7-methyl spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′,7-dicarboxylate (3.5 g, 8.8 mmol) in LiOH (18 mL of 2.0 M, 35.1 mmol) and dioxane (18 mL) was stirred at 55° C. for 1 hour. The reaction mixture was diluted with ethyl acetate and was washed with water. The aqueous layer was acidified with 1N HCl and the product was extracted into ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated to yield 1′-(tert-butoxycarbonyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-7-carboxylic acid which was used without further purification. ESI-MS m/z calc. 384.4. found 385.3 (M+1)+. Retention time: 1.81 minutes (3 min run).

Workup

  1. washwas washed with water
  2. extractionthe product was extracted into ethyl acetate
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-4f042f36be38488e99e11a8cbc957592
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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