Réaction #324446

ord-117276b226d84d848f6f10d7d11df6db

Équation de réaction

O=S(=O)([O-])O.[K+]
KHSO4
COC(=O)C(Oc1ccc(Cl)cc1OC1CN(C(=O)OC(C)(C)C)C1)c1ccccc1
title compound
COC(=O)C(Oc1ccc(Cl)cc1OC1CN(C(=O)OC(C)(C)C)C1)c1ccccc1
3-[5-Chloro-2-(methoxycarbonyl-phenyl-methoxy)-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester
[Na+].[OH-]
NaOH
CC(C)(C)OC(=O)N1CC(Oc2cc(Cl)ccc2OC(C(=O)O)c2ccccc2)C1
title compound
Rendement 102.4%
CC(C)(C)OC(=O)N1CC(Oc2cc(Cl)ccc2OC(C(=O)O)c2ccccc2)C1
3-[2-(Carboxy-phenyl-methoxy)-5-chloro-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester
Rendement 102.4%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Extractionextracted with EtOAc (2×)
  2. 2
    LavageThe combined organics were washed with brine
  3. 3
    Autredried

Mode opératoire

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08642583B2uspto-grants-2014_02