(S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate → HCID 11165987, compound

HRID 58312Notes

Reaction equation

HRID 58312 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][CH2:4][C:5](=[O:8])[O:6][CH3:7]>C(#N)C.CN(C1C=CN=CC=1)C>[C:19]([O:18][C:16]([N:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@@H:2]([CH2:3][CH2:4][C:5]([O:6][CH3:7])=[O:8])[C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 1

HCID 11120686(S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate

Product 1

HCID 11165987HCID 11165987, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Procedure

13.4 g of Boc-Glu(OMe)-OtBu (˜39.6 mmol) are dissolved in 30 mL of acetonitrile and treated with 986 mg of DMAP (7.91 mmol, 0.2 eq). Under nitrogen atmosphere a solution of 17.6 g of di-tert-butylbicarbonate (77.1 mmol, 2 eq) in 100 mL of acetonitrile is added. After stirring overnight, the solvent is removed in vacuo and the obtained crude product is purified by chromatography on silica gel (column: 31*6.0 cm, petroleum ether/ethyl acetate 9:1)

Workup

  1. customthe solvent is removed in vacuo
  2. customthe obtained crude product
  3. customis purified by chromatography on silica gel (column: 31*6.0 cm, petroleum ether/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-2ef8a1f1cc834a6ab46872f54f5af694
Source dataset
uspto-grants-2016_09
Patent number
US09434763B2

Reaction notes

Loading…