Trifluoroacetic acid → HCID 67113963, compound

HRID 331094Notes

Reaction equation

HRID 331094 reaction equation
[OH:1][C:2]1([CH2:17][CH:18]=O)[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[C:20](=[O:27])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[NH2:21].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[C:23]([O:22][C:20]([NH:21][CH2:18][CH2:17][C:2]1([OH:1])[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])=[O:27])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 77922tert-Butyl carbamateHCID 86668861HCID 86668861, compound

Product 1

HCID 67113963HCID 67113963, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of benzyl 2-hydroxy-2-(2-oxoethyl)cyclopentanecarboxylate (from step C, 120 mg, 0.457 mmol) in acetonitrile (2 mL) was added tert-butyl carbamate (214 mg, 1.830 mmol), triethylsilane (213 mg, 1.830 mmol) and trifluoroacetic acid (0.070 mL, 0.915 mmol). The resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and subjected to preparative HPLC(Shimadzu VP-ODS 20×100 mm, 8 min. gradient, Solvent A: 10% MeOH, 90% H2O, 0.1% TFA; Solvent B: 90% MeOH, 10% H2O, 0.1% TFA; wavelength: 220 nM). The desired fractions were concentrated and freeze dried to yield benzyl 2-(2-(tert-butoxycarbonylamino)ethyl)-2-hydroxycyclopentanecarboxylate (70 mg, 0.193 mmol, 42.1% yield) as a solid. MS (ESI+)=386 (M+Na)+

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customsubjected to preparative HPLC(Shimadzu VP-ODS 20×100 mm, 8 min. gradient, Solvent A
  3. concentrationThe desired fractions were concentrated
  4. customfreeze dried

Sources & evidence

ORD record
ord-434471025dd74a438f11e634a0b7ab3b
Source dataset
uspto-grants-2014_11
Patent number
US08877749B2

Reaction notes

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