Sodium hydride → HCID 58405064, compound

HRID 237273Notes

Reaction equation

HRID 237273 reaction equation
C(OC([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][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[CH2:9]1)=O)(C)(C)C.C(OC(N1CC(OC2C=C(Cl)C=CC=2O)C1)=O)(C)(C)C.[H-].[Na+]>CN(C=O)C>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]([O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)=[C:13]([CH:18]=1)[O:12][CH:10]1[CH2:9][NH:8][CH2:11]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 673429093-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl esterHCID 673491211,1-Dimethylethyl 3-[5-chloro-2-[2-(3-chlorophenyl)ethoxy]phenoxy]-1-azetidinecarboxylate

Product 1

HCID 58405064HCID 58405064, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation of 3-[5-Chloro-2-[2-(3-chloro-phenyl)-ethoxy]-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester. To a solution of 3-(5-chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (60 mg, 0.20 mmol) in DMF (2 mL) was added NaH (10 mg, 0.24 mmol). After 5 min, the title compound of Step A (56 mg, 0.24 mmol) was added and the resulting mixture was heated at 65° C. for 18 h. The reaction was diluted with H2O and extracted EtOAc (3×). The organics were dried and purified by RP HPLC (Agilent) to give the title compound as an oil (47 mg, 54%). MS (ESI): mass calcd. for C22H25Cl2NO4, 438.3; m/z found, 382.0 [M-56+H]+. 1H NMR (CDCl3): 7.34-7.32 (m, 1H), 7.25-7.22 (m, 2H), 7.19-7.16 (m, 1H), 6.90 (dd, J=8.8, 2.0 Hz, 1H), 6.78 (d, J=8.8 Hz, 1H), 6.54 (d, J=2.4 Hz, 1H), 4.85-4.79 (m, 1H), 4.30-4.25 (m, 2H), 4.16 (t, J=6.7 Hz, 2H), 4.07-4.03 (m, 2H), 3.10 (t, J=6.7 Hz, 2H), 1.46 (s, 9H).

Sources & evidence

ORD record
ord-987d1ee8e5a14dcaac2efa1713bccd7d
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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