Trifluoroacetic acid → HCID 71748114, compound

HRID 2277093Notes

Reaction equation

HRID 2277093 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][NH:14]C(=O)OC(C)(C)C)=[C:11]([CH2:24][NH:25][C:26]([C@@H:28]2[CH2:33][N:32]([CH3:34])[CH2:31][CH2:30][N:29]2[C:35](=[O:42])[C@H:36]([OH:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[O:27])[CH:10]=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:14][CH2:13][C:12]1[CH:22]=[CH:23][C:9]([Cl:8])=[CH:10][C:11]=1[CH2:24][NH:25][C:26]([C@@H:28]1[CH2:33][N:32]([CH3:34])[CH2:31][CH2:30][N:29]1[C:35](=[O:42])[C@H:36]([OH:41])[C:37]([CH3:39])([CH3:40])[CH3:38])=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89824785HCID 89824785, compound

Product 1

HCID 71748114HCID 71748114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL, 50% solution in CH2Cl2) was added to a solution of tert-Butyl 4-chloro-2-[{(S)-1-{(R)-2-hydroxy-3,3-dimethylbutanoyl}-4-methylpiperazine-2-carboxamido}methyl]benzylcarbamate (0.022 g, 0.0043 mmol) in CH2Cl2 (1 mL) and the reaction mixture was stirred under nitrogen for 1 h. The solvent was removed at reduced pressure and the residue was azeotroped with toluene (5 mL). The solid was washed with ether (2×4 mL) and dried under high vacuum to afford the title compound as a white hygroscopic solid. 1H NMR (MeOD-d4, 300 MHZ) (δ) ppm: 7.36-7.55 (m, 3H), 5.21-5.38 (m, 1H), 4.37-4.53 (m, 3H), 4.26-4.28 (m, 3H), 3.95-3.68 (m, 2H), 3.16-3.22 (m, 1H), 2.55-2.73 (m, 5H), 0.97 (s, 9H).

Workup

  1. customThe solvent was removed at reduced pressure
  2. customthe residue was azeotroped with toluene (5 mL)
  3. washThe solid was washed with ether (2×4 mL)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-db428da0fef442c1be0187f485e82ad8
Source dataset
uspto-grants-2015_09
Patent number
US09133147B2

Reaction notes

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