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Trifluoroacetic acid → (R)-2-amino-1-(3-fluoro-azetidin-1-yl)-3-methoxy-propan-1-one trifluoroacetate

HRID 246168
Notes
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Reaction equation

HRID 246168 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:16][O:17][CH3:18])[C:9]([N:11]1[CH2:14][CH:13]([F:15])[CH2:12]1)=[O:10])(C)(C)C.[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23]>ClCCl>[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23].[NH2:7][C@H:8]([CH2:16][O:17][CH3:18])[C:9]([N:11]1[CH2:14][CH:13]([F:15])[CH2:12]1)=[O:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71279849[(R)-2-(3-fluoro-azetidin-1-yl)-1-methoxymethyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 71280390(R)-2-amino-1-(3-fluoro-azetidin-1-yl)-3-methoxy-propan-1-one trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 25 mL round-bottomed flask, [(R)-2-(3-fluoro-azetidin-1-yl)-1-methoxymethyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (265 mg, 0.96 mmol) was dissolved in dichloromethane (5 ml). The reaction was cooled to 0° C. and trifluoroacetic acid (1.5 ml, 19.5 mmol) was slowly added. The reaction mixture was stirred at room temperature for 3 h then concentrated to provide (R)-2-amino-1-(3-fluoro-azetidin-1-yl)-3-methoxy-propan-1-one trifluoroacetate as a colorless viscous oil which was used without further purification.

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-6a8c9f3b511b4320a8a7679fc19978c0
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658646B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes