Trifluoroacetic acid → HCID 21990122, compound

HRID 1825068Notes

Reaction equation

HRID 1825068 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)=O)(C)(C)C.[F:13][C:14]([F:19])([F:18])[C:15]([OH:17])=[O:16]>C(Cl)Cl>[F:13][C:14]([F:19])([F:18])[C:15]([OH:17])=[O:16].[NH:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 21990122HCID 21990122, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Hydroxy-azetidine-1-carboxylic acid tert-butyl ester 9b (0.73 g, 4.2 mmole) was dissolved in CH2Cl2 (2 ml) and trifluoroacetic acid (2 ml). CAUTION: The deprotection generated a rapid evolution of gas. The clear solution was stirred for 75 minutes and the solvent was removed, in vacuo, to a clear oil (1.4 g, >100%): 1H-NMR (DMSO-d6, 400 MHz) δ 8.63 (2H, br. s), 4.55–4.48 (1H, m), 4.09–4.02 (2H, m), 3.76–3.68 (2H, m).

Workup

  1. customthe solvent was removed, in vacuo, to a clear oil (1.4 g, >100%)

Sources & evidence

ORD record
ord-f14ca232dd0a428dab2418400a3e48d7
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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