Trifluoroacetic acid → 3(S)-amino-2(S)-hydroxyheptanoic acid trifluoroacetate

HRID 635637Notes

Reaction equation

HRID 635637 reaction equation
[NH2:1][C@@H:2]([CH2:12][CH2:13][CH2:14][CH3:15])[C@H:3]([OH:11])[C:4]([O:6]C(C)(C)C)=[O:5].[F:16][C:17]([F:22])([F:21])[C:18]([OH:20])=[O:19]>>[F:16][C:17]([F:22])([F:21])[C:18]([OH:20])=[O:19].[NH2:1][C@@H:2]([CH2:12][CH2:13][CH2:14][CH3:15])[C@H:3]([OH:11])[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20639995tert-butyl 3(S)-amino-2(S)-hydroxyheptanoate

Product 1

HCID 867564193(S)-amino-2(S)-hydroxyheptanoic acid trifluoroacetate

Procedure

0.26 g of tert-butyl 3(S)-amino-2(S)-hydroxyheptanoate was treated with 2 ml of trifluoroacetic acid for 30 minutes. The trifluoroacetic acid was evaporated and the residue was evaporated twice with toluene. Trituration with diethyl ether gave 0.155 g of 3(S)-amino-2(S)-hydroxyheptanoic acid trifluoroacetate as a white solid, MS: m/e 162 [M+H]+.

Workup

  1. customThe trifluoroacetic acid was evaporated
  2. customthe residue was evaporated twice with toluene

Sources & evidence

ORD record
ord-e3d78c5649944fd3998bd6fc45def16e
Source dataset
uspto-grants-2001_02
Patent number
US06187905B1

Reaction notes

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