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 1908150Notes

Reaction equation

HRID 1908150 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-6e36b3fae68840328e165620b75f14ae
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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