Trifluoroacetic acid → HCID 86705544, compound

HRID 2279555Notes

Reaction equation

HRID 2279555 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([C:8]([O:10][C@H:11]([CH3:29])[C@@H:12]([NH:21]C(OC(C)(C)C)=O)[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][C@H:11]([CH3:29])[C@@H:12]([NH2:21])[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=2)=[O:9])=[CH:30][CH:31]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86705545HCID 86705545, compound

Product 1

HCID 86705544HCID 86705544, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 332 (103 mg, 0.227 mmol) in DCM (2.2 mL) at RT under nitrogen was added TFA (1 mL). After 2 h the reaction was concentrated to dryness in a rotovap and high vacuum. The crude presumed TFA salt was redissolved in DCM (5 mL) and stirred rapidly with 10% aqueous Na2CO3 (5 mL). After 5 min the organics phase was separated, dried (MgSO4), filtered and concentrated to afford 80 mg (100%) of (1S,2R)-1-amino-1-(3-chloro-4-fluorophenyl)propan-2-yl 4-nitrobenzoate (334) as a yellow oil which was used without additional purification.

Workup

  1. concentrationAfter 2 h the reaction was concentrated to dryness in a rotovap and high vacuum
  2. dissolutionwas redissolved in DCM (5 mL)
  3. customAfter 5 min the organics phase was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d8d69a7af54b4a2e829fe3c9dfb6fcc7
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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