Trifluoroacetic acid → methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate

HRID 929402

Reaction equation

HRID 929402 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:18]([O:20][CH3:21])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C@@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11132998Boc-L-Lys(Z)-OMe

Product 1

HCID 6994982methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-L-Lys(Z)OMe 31 (2.00 g, 12.6 mmol) in DCM (30 mL) was added 30 mL of TFA. The mixture was stirred at rt for 1 h. Then the solvent were removed in vacuo, the residue was coevaporated 3 times with toluene. The residue was precipitated in Et2O to give the subject compound (2.1 g, yield 100%). Intermediate 32 was characterized by the following spectroscopic data: 1H NMR (DMSO-d6, 300 MHz) δ (ppm) 8.45 (sl, 2H), 7.33 (m, 5H), 7.31 (t, 1H), 5.00 (s, 2H), 4.03 (m, 1H), 3.74 (s, 3H), 2.97 (m, 2H), 1.75 (m, 2H), 1.39 (m, 4H).

Workup

  1. customThen the solvent were removed in vacuo
  2. customThe residue was precipitated in Et2O

Sources & evidence

ORD record
ord-ad81102993b0411b960455323fc478eb
Source dataset
uspto-grants-2016_03
Patent number
US09295732B2

Linked notes

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