Water → HCID 87364079, compound

HRID 1850092Notes

Reaction equation

HRID 1850092 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[OH:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[O:28](S(C(F)(F)F)(=O)=O)[S:29]([C:32]([F:35])([F:34])[F:33])(=O)=[O:30].O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([O:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[O:20][S:29]([C:32]([F:35])([F:34])[F:33])(=[O:30])=[O:28])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 673429093-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 87364079HCID 87364079, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-(5-chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (2.0 g, 6.7 mmol) in CH2Cl2 (34 mL) at 0° C. was added Et3N (0.74 g, 1.0 mL, 7.3 mmol) and Tf2O (2.0 g, 7.0 mmol). After warming to rt, H2O was added and the mixture extracted with CH2Cl2 (2×). The combined organics were dried. Silica gel chromatography (5-25%) gave 1.12 g (39%) of the title compound as a white solid. 1H NMR (CDCl3): 7.20 (d, J=8.7 Hz, 1H), 7.03 (dd, J=8.7, 2.3 Hz, 1H), 6.67 (d, J=2.3 Hz, 1H), 4.95-4.91 (m, 1H), 4.34 (ddd, J=10.0, 6.4, 1.0 Hz, 2H), 4.08-4.04 (m, 2H), 1.46 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-c254e30a0e21498aaf8de0b54ee98c70
Source dataset
uspto-grants-2015_02
Patent number
US08957059B2

Reaction notes

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