Trifluoroacetic acid → HCID 25418061, compound

HRID 2245450Notes

Reaction equation

HRID 2245450 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2CNC(=O)OC(C)(C)C)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>ClCCl>[NH:14]1[CH2:15][CH2:16][CH2:17][C@@H:13]1[CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86761069HCID 86761069, compound

Product 1

HCID 25418061HCID 25418061, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl (2R)-2-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinylmethylcarbamate (D108, 2.07 g, 6.1 mmol) in 16 ml of dichloromethane, cooled to 0° C., were added 4 ml of TFA. The reaction mixture was allowed to warm-up to r.t. and then it was stirred at this temperature for 30 mins. The title compound (1.06 g, y=88%) was isolated after purification by SCX. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.00-7.66 (m, 5 H) 4.90-5.20 (m, 2 H) 3.12-3.24 (m, 1 H) 2.97-3.09 (m, 1 H) 2.84-2.97 (m, 2 H) 2.61-2.82 (m, 2 H) 1.44-1.83 (m, 3 H) 1.14-1.40 (m, 1 H)

Sources & evidence

ORD record
ord-5def418aea874e81af0e11545dbf0dd1
Source dataset
uspto-grants-2010_03
Patent number
US07683056B2

Reaction notes

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