Trifluoroacetic acid → HCID 58017544, compound

HRID 1642767Notes

Reaction equation

HRID 1642767 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:24]2[CH:28]=[N:27][N:26]=[N:25]2)=[C:6]([CH:23]=1)[CH2:7][NH:8][C:9]([C@@H:11]1[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[NH:12]1)=[O:10].[C:29]1([C@@H:35]([O:39][Si](C)(C)C)[C:36](Cl)=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:24]2[CH:28]=[N:27][N:26]=[N:25]2)=[C:6]([CH:23]=1)[CH2:7][NH:8][C:9]([C@@H:11]1[CH2:15][CH2:14][NH:13][N:12]1[C:36](=[O:37])[C@H:35]([OH:39])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:10]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 58017559HCID 58017559, compoundHCID 86637427HCID 86637427, compound

Product 1

HCID 58017544HCID 58017544, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3S)-3-{[5-chloro-2-(1H-tetrazol-1-yl)benzyl]carbamoyl}pyrazolidine-1-carboxylate (82 mg, 0.200 mmol) in DCM (2 mL) and pyridine (0.080 mL) was added a solution of (R)-2-phenyl-2-(trimethylsilyloxy)acetyl chloride (ca 0.3 M in DCM, 1 mL, 0.3 mmol, see Preparation 2). The resulting solution was stirred at rt over night. TFA (ca 1 mL) was added and the mixture was stirred for one more hour and then evaporated. The residue was purified using flash chromatography (DCM/MeCN gradient from 2:1 to 1:1) to give (3S)—N-[5-chloro-2-(1H-tetrazol-1-yl)benzyl]-2-[(2R)-2-hydroxy-2-phenylacetyl]pyrazolidine-3-carboxamide (52 mg, 59%) as an oil.

Workup

  1. stirringthe mixture was stirred for one more hour
  2. customevaporated
  3. customThe residue was purified

Sources & evidence

ORD record
ord-31976b3e3c374c3eb5e662b636b618b5
Source dataset
uspto-grants-2012_02
Patent number
US08119673B2

Reaction notes

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