Lithium Hydroxide → 2-(2-Methoxy-4-(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-ylcarbonyl)phenoxy)acetic acid

HRID 2204245Notes

Reaction equation

HRID 2204245 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[C:13]([C:15]([N:17]2[CH2:22][CH2:21][C:20]3([O:27][C:26]4[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=4[N:24]4[CH:32]=[CH:33][CH:34]=[C:23]34)[CH2:19][CH2:18]2)=[O:16])[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][C:7]([O:9]C)=[O:8].[Li+].[OH-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:14]=[C:13]([C:15]([N:17]2[CH2:18][CH2:19][C:20]3([O:27][C:26]4[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=4[N:24]4[CH:32]=[CH:33][CH:34]=[C:23]34)[CH2:21][CH2:22]2)=[O:16])[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58550733Methyl 2-(2-methoxy-4-(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-ylcarbonyl)phenoxy)acetate

Product 1

HCID 585515612-(2-Methoxy-4-(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-ylcarbonyl)phenoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(2-methoxy-4-(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-ylcarbonyl)phenoxy)acetate (140 mg, 0.303 mmol) in THF (4 mL) was added LiOH (600 μL of 2.0 M, 1.2 mmol) and the mixture was stirred at room temperature for 19 h. The mixture was filtered and was purified by HPLC using 5 mM HCl/water and MeOH to yield 2-(2-methoxy-4-(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-ylcarbonyl)phenoxy)acetic acid. ESI-MS m/z calc. 448.2, found 449.3 (M+1)+; Retention time: 5.90 minutes (15 min run).

Workup

  1. filtrationThe mixture was filtered
  2. customwas purified by HPLC

Sources & evidence

ORD record
ord-7a8963183b354c19ae592db330e1b448
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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