Dichloromethane → 3-(2-Carboxymethoxy-5-chloro-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

HRID 237307Notes

Reaction equation

HRID 237307 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][CH2:21][C:22]([O:24]CC)=[O:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(Cl)Cl.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][CH2:21][C:22]([OH:24])=[O:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 673467163-(5-Chloro-2-ethoxycarbonylmethoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 673480503-(2-Carboxymethoxy-5-chloro-phenoxy)-azetidine-1-carboxylic acid tert-butyl esterYield 57.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the title compound from Step A (1.70 g, 4.40 mmol) in MeOH (10 mL) was added 4N NaOH (10 mL). After 2 h, CH2Cl2 was added and the mixture acidified with 1N KHSO4 (50 mL) then extracted with CH2Cl2 (2×). The combined organics were dried to give a 0.90 g (57%) of the title compound as a white solid that was used without further purification. MS (ESI): mass calcd. for C16H20ClNO6, 357.1; m/z found, 380.1 [M+Na]+. 1H NMR (400 MHz): 6.92 (dd, J=8.6, 2.3 Hz, 1H), 6.85 (d, J=8.7 Hz, 1H), 6.59 (d, J=2.3 Hz, 1H), 4.92-4.86 (m, 1H), 4.67 (s, 2H), 4.31 (dd, J=9.9, 6.5 Hz, 2H), 4.07 (dd, J=10.0, 4.1 Hz, 2H), 1.45 (s, 9H).

Workup

  1. extractionthen extracted with CH2Cl2 (2×)
  2. customThe combined organics were dried

Sources & evidence

ORD record
ord-a2257dd5a2f24ddda811b8f61824283e
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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