Hydrochloric Acid → HCID 67347021, compound

HRID 237260Notes

Reaction equation

HRID 237260 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[OH:20])[CH2:9]1)=O)(C)(C)C.Cl>CCOC(C)=O.O1CCOCC1>[ClH:19].[NH: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

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 673429093-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67347021HCID 67347021, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To 3-(5-Chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (0.80 g, 2.7 mmol) in EtOAc (2 mL) was added 4M HCl in dioxane (5 mL). After 18 h, EtOAc was added and the resulting white solid filtered to give 2-(azetidin-3-yloxy)-4-chloro-phenol hydrochloride as a white solid. To a CH2Cl2 (25 mL) solution of this compound was added Et3N (0.30 g, 0.42 mL, 3.0 mmol) and TFAA (0.58 g, 0.38 mL, 2.8 mmol). After 18 h, H2O was added and the reaction extracted with CH2Cl2 (2×). The combined organics were dried and concentrated to give 0.54 g (74% yield 2 steps) of the title compound as a brown oil that was used in the next step without further purification.

Workup

  1. filtrationthe resulting white solid filtered

Sources & evidence

ORD record
ord-07e2255f90bc4030a1402b21bfb6d25d
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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