Trifluoroacetic acid → HCID 131732402, compound

HRID 1430931Notes

Reaction equation

HRID 1430931 reaction equation
C([NH:8][C:9]1[C:10]([Cl:37])=[C:11]([N:18]2[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:28])[O:26][CH3:27])[C@@H:20]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:19]2)[CH:12]=[C:13]([C:15](=[O:17])[NH2:16])[CH:14]=1)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)CCl>[NH2:8][C:9]1[C:10]([Cl:37])=[C:11]([N:18]2[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:28])[O:26][CH3:27])[C@@H:20]([O:29][Si:30]([C:33]([CH3:35])([CH3:34])[CH3:36])([CH3:31])[CH3:32])[CH2:19]2)[CH:12]=[C:13]([C:15](=[O:17])[NH2:16])[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131732403HCID 131732403, compound

Product 1

HCID 131732402HCID 131732402, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

methyl ((3S,4S)-1-(3-(N-BOC-amino)-5-carbamoyl-2-chlorophenyl)-3-((tert-butyldimethylsilyl)oxy)piperidin-4-yl)carbamate (125 mg, 0.168 mmol) was dissolved in ClCH2CH2Cl (10 ml). Trifluoroacetic acid (3 ml, 38.9 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours, then evaporated to dryness. The crude was purified by column chromatography on silica (40 g cartridge, gradient from 100% DCM to 100% EtOAc, then hold at 100% EtOAc) to give methyl ((3S,4S)-1-(3-amino-5-carbamoyl-2-chlorophenyl)-3-((tert-butyldimethylsilyl)oxy)piperidin-4-yl)carbamate (67 mg).

Workup

  1. customevaporated to dryness
  2. customThe crude was purified by column chromatography on silica (40 g cartridge, gradient from 100% DCM to 100% EtOAc

Sources & evidence

ORD record
ord-25a9ff84fa974bea930c8d12fff1d501
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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