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

HRID 1945050Notes

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]

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. additionMethylene chloride is added
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-5735bac5e33c42fc8bebd19bd510b6c2
Source dataset
uspto-grants-2013_03
Patent number
US08394853B2

Reaction notes

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