Trifluoroacetic acid → HCID 57999691, compound

HRID 600339Notes

Reaction equation

HRID 600339 reaction equation
[NH2:1][C:2](=[O:28])[C@@H:3]([NH:20]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:20][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)[C:2]([NH2:1])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57999655(S)-tert-butyl 1-amino-1-oxo-3-(4-(phenylsulfonyl)phenyl)propan-2-ylcarbamate

Product 1

HCID 57999691HCID 57999691, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-tert-butyl 1-amino-1-oxo-3-(4-(phenylsulfonyl)phenyl)propan-2-ylcarbamate (440 mg) in DCM (10 mL) at 0° C. was added TFA (2.51 mL). The mixture was allowed to warm to RT and stirred for 1 h. The mixture was concentrated in vacuo and partitioned between saturated aqueous sodium bicarbonate and ethyl acetate, dried over sodium sulfate, filtered and concentrated in vacuo to leave the subtitle compound (175 mg) as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-775f7b830b52419fa054822d94704055
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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