Trifluoroacetic acid → 2,2'-{[6-(Benzyloxy)-6-oxohexanoyl]imino}diacetic acid

HRID 1488249Notes

Reaction equation

HRID 1488249 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][N:8]([CH2:25][C:26](=[O:32])[O:27]C(C)(C)C)[C:9](=[O:24])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([N:8]([CH2:25][C:26]([OH:32])=[O:27])[CH2:7][C:6]([OH:33])=[O:5])=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117995888Benzyl 6-[bis(2-tert-butoxy-2-oxoethyl)amino]-6-oxohexanoate

Product 1

HCID 1179960702,2'-{[6-(Benzyloxy)-6-oxohexanoyl]imino}diacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of benzyl 6-[bis(2-tert-butoxy-2-oxoethyl)amino]-6-oxohexanoate (5.9 g, 12.73 mmol) in CH2Cl2 (30 mL) at room temperature was added TFA (30 mL, 12.73 mmol). After stirring at room temperature for 16 hours, the mixture was concentrated. The residue was purified by flash chromatography on C18 reverse phase silica gel to give the title compound. LC-MS Method A: m/e=486 [M+1]; Rt=2.53 min. 1H NMR (CD3OD) δ 7.30 (m, 5H), 5.06 (s, 2H), 4.81 (s, 4H), 4.19 (s, 2H), 4.07 (s, 2H), 2.34 (q, 4H, J=7.03).

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by flash chromatography on C18 reverse phase silica gel

Sources & evidence

ORD record
ord-217a5f354ec14d76a3f656ef499e902c
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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