Trifluoroacetic acid → 1-(Naphthalene-1-ylcarbonyl)-L-Proline

HRID 244247Notes

Reaction equation

HRID 244247 reaction equation
C([O:5][C:6](=[O:24])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:13])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:14]1([C:12]([N:8]2[CH2:9][CH2:10][CH2:11][C@H:7]2[C:6]([OH:24])=[O:5])=[O:13])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89969811tert-Butyl-1(naphthalene-1-ylcarbonyl)-L-Prolinate

Product 1

HCID 104921841-(Naphthalene-1-ylcarbonyl)-L-ProlineYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To compound 19 (550 mg, 1.7 mmol) was added a solution of TFA in dichloromethane (95:5, v/v) (4.0 mL). The solution was stirred over a period of 4 h at room temperature under an argon atmosphere. The resulting solution was evaporated under reduced pressure and purified by FCC (CH2Cl2/MeOH, 95:5) to give 415 mg (89%) of title compound 20. 1H NMR (acetone-d6) δ: 2.00 and 2.35 (2m, 3.2 H and 0.8 H, 2×CH2 of proline), 3.66 and 3.74 (2m, 1.6H and 0.4H, CH2N of proline), 4.60 and 4.67 (m, 0.2H and 0.8H, NCHCO of proline), 7.57 (broad, m, 2×CH of naphthalene), 7.67 (d, J=8.4 Hz, 1×CH of naphthalene), 7.95 (broad, m, 2×CH of naphthalene), 8.14 (s, 1×CH of naphthalene). LRMS for C16H16NO3 [M+H]+: 270.0 m/z.

Workup

  1. customThe resulting solution was evaporated under reduced pressure
  2. custompurified by FCC (CH2Cl2/MeOH, 95:5)

Sources & evidence

ORD record
ord-b9151ce9f4ba4297b8c205ac8d5ba44c
Source dataset
uspto-grants-2014_02
Patent number
US08653054B2

Reaction notes

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