1,2-Dichloroethane → Benzyl 6-[bis(2-tert-butoxy-2-oxoethyl)amino]-6-oxohexanoate

HRID 1488248Notes

Reaction equation

HRID 1488248 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH:41]([CH2:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>CN(C=O)C.O>[C:46]([O:45][C:43](=[O:44])[CH2:42][N:41]([CH2:50][C:51](=[O:52])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:17])([CH3:49])([CH3:47])[CH3:48]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4393691DI-T-Butyl iminodiacetateHCID 11075409Adipic acid monobenzyl ester

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-(benzyloxy)-6-oxohexanoic acid (1.5 g, 6.35 mmol) in DMF (50 mL) at room temperature was added DIPEA (2.218 mL, 12.70 mmol), HOBt (1.945 g, 12.7 mmol), EDC (2.434 g, 12.7 mmol) and di-tert-butyl 2,2′-iminodiacetate (2.34 g, 9.52 mmol). After stirring at room temperature for 16 hours, the reaction mixture was diluted with H2O (30 mL) and extracted with CH2Cl2 (2×30 mL). The combined organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on silica gel (80 g), eluting with 0-40% EtOAc in hexane, to give the title compound. LC-MS Method A: m/e=464.04 [M+1]; Rt=2.47 min. 1H NMR (CDCl3) δ 7.32 (m, 5H), 5.07 (s, 2H), 4.02 (s, 2H), 3.96 (s, 2H), 2.35 (s, 2H), 2.26 (s, 2H), 1.66 (s, 4H), 1.42-1.44 (bs, 18H).

Workup

  1. extractionextracted with CH2Cl2 (2×30 mL)
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (80 g)
  6. washeluting with 0-40% EtOAc in hexane

Sources & evidence

ORD record
ord-a1fc44b91ad547a2ae5093f90d7d7ef2
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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