Sodium Hydroxide → 3-[2-(Carboxy-phenyl-methoxy)-5-chloro-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester

HRID 237264Notes

Reaction equation

HRID 237264 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH:21]([C:28]([O:30]C)=[O:29])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].OS([O-])(=O)=O.[K+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][CH:21]([C:28]([OH:30])=[O:29])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 67346530HCID 67346530, compound

Product 1

HCID 673485773-[2-(Carboxy-phenyl-methoxy)-5-chloro-phenoxy]-azetidine-1-carboxylic acid tert-butyl esterYield 102.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the title compound of Example 148 Step A (0.16 g, 0.36 mmol) in MeOH (3 mL) was added 1N NaOH (3 mL). After 18 h, the solution was acidified with 1N KHSO4 and extracted with EtOAc (2×). The combined organics were washed with brine and dried to give 0.16 g (>98%) of the title compound. 1H NMR (CDCl3): 8.56-8.19 (broad s, 1H), 7.55-7.51 (m, 2H), 7.41-7.36 (m, 3H), 6.85-6.84 (m, 2H), 6.54 (s, 1H), 5.55 (s, 1H), 4.88-4.83 (m, 1H), 4.29-4.24 (m, 2H), 4.06-3.97 (m, 2H), 1.44 (s, 9H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organics were washed with brine
  3. customdried

Sources & evidence

ORD record
ord-117276b226d84d848f6f10d7d11df6db
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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