Trifluoroacetic acid → Trifluoroacetic acid

HRID 1368869Notes

Reaction equation

HRID 1368869 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([P:14]([OH:33])([O:16][C@@H:17]([CH2:21][CH2:22][CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)[C:18]([OH:20])=[O:19])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>ClCCl>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[NH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C@H:17]([O:16][P:14]([C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:13])([OH:33])=[O:15])[C:18]([OH:20])=[O:19]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 20592175HCID 20592175, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 12989017HCID 12989017, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A dichloromethane (0.5 ml) suspension of the (S)-2-(((R)-1-(benzyloxycarbonylamino)ethyl)(hydroxyphosphinoyl)oxy)-6-(tert-butoxycarbonylamino)hexanoic acid (3.1 mg) obtained in the above step (b) was added with anisol (0.05 ml) and trifluoroacetic acid (0.5 ml) at 0° C., and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was concentrated, and the residue was washed with isopropyl ether to obtain trifluoroacetic acid salt of the title compound: (S)-6-amino-2-(((R)-1-(benzyloxycarbonylamino)ethyl)(hydroxyphosphinoyl)oxy)hexanoic acid (3.0 mg, 94%).

Workup

  1. customobtained in the above step (b)
  2. concentrationThe reaction mixture was concentrated
  3. washthe residue was washed with isopropyl ether

Sources & evidence

ORD record
ord-e257737ddea8458a817d261a34b0abb6
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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