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Trifluoroacetic acid → (2R,4R)-4-amino-2-methyl-pentanoic acid ethyl ester trifluoroacetate

HRID 1945050
Notes
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Reaction equation

HRID 1945050 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C@H:5]([CH3:17])[CH2:6][C@H:7]([NH:9]C(OC(C)(C)C)=O)[CH3:8])[CH3:2].[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22]>>[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].[CH2:1]([O:3][C:4](=[O:18])[C@H:5]([CH3:17])[CH2:6][C@H:7]([NH2:9])[CH3:8])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86648195(2R,4R)-4-tert-butoxycarbonylamino-2-methyl-pentanoic acid ethyl ester

Product 1

HCID 86648194(2R,4R)-4-amino-2-methyl-pentanoic acid ethyl ester trifluoroacetate

Procedure

Next, (2R,4R)-4-tert-butoxycarbonylamino-2-methyl-pentanoic acid ethyl ester (142 mg, 0.548 mmol) is added to trifluoroacetic acid (5 mL). After 10 minutes, the solvent is removed under reduced pressure. Methylene chloride is added and the solvent is removed under reduced pressure to give (2R,4R)-4-amino-2-methyl-pentanoic acid ethyl ester trifluoroacetate. This material is used directly in the subsequent coupling reaction.

Workup

  1. customthe solvent is removed under reduced pressure
  2. addition
Methylene chloride is added
  • customthe solvent is removed under reduced pressure
  • Sources & evidence

    ORD record
    ord-5735bac5e33c42fc8bebd19bd510b6c2
    Source dataset
    uspto-grants-2013_03
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08394853B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes