Trifluoroacetic acid → Trifluoroacetic acid

HRID 1582585Notes

Reaction equation

HRID 1582585 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, 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-c42e0577262b4eae91a19af16fd4ad63
Source dataset
uspto-grants-2004_05
Patent number
US06737416B2

Reaction notes

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