Dicyclohexylcarbodiimide → HCID 86584774, compound

HRID 1166450Notes

Reaction equation

HRID 1166450 reaction equation
[C:1]([NH:8][C@H](C(O)=O)CC)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[N:16]1[C:21](=[O:22])[CH2:20][CH2:19][C:17]1=O.[CH2:23]1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[CH3:23][C@@H:20]([CH:19]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH3:17])[C:21]([NH2:16])=[O:22]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 2755934(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acid

Product 1

HCID 86584774HCID 86584774, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

BOC-homoalanine (Podlech, J.; Seebach, D. (1995) Liebigs Ann. 1217) (0.44 g, 2.17 mmol) was dissolved in 5 mL methylene chloride. HOSu (376.4 mg, 3.27 mmol) was added and the solution cooled to 0° C. After addition of DCC (587.8 mg, 2.85 mmol) the solution was stirred 1 hour at 0° C., warmed to room temperature and stirred for an additional 2 hours. A stream of methylamine was bubbled through the suspension for 10 minutes, and stirring was continued overnight. The white precipitate was filtered off by suction filtration and the filtrate concentrated to give a pale yellow solid that was purified by chromatography (silica gel, CHCl3/MeOH 19:1) to yield 0.41 g (1.90 mmol, 88%) Of BOC-homoalanine methylamide (18) as a white solid. 1H-NMR (300 MHz, CDCl3) δ 6.11 (b, NH), 5.23 (b, NH), 3.92 (m, 1H), 2.75 (d, J=4.8 Hz, 3H), 2.35 (m, 2H), 1.39 (s, 9H), 1.17 (d, J=6.6 Hz, 3H).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for an additional 2 hours
  3. customA stream of methylamine was bubbled through the suspension for 10 minutes
  4. stirringstirring
  5. waitwas continued overnight
  6. filtrationThe white precipitate was filtered off by suction filtration
  7. concentrationthe filtrate concentrated
  8. customto give a pale yellow solid
  9. customthat was purified by chromatography (silica gel, CHCl3/MeOH 19:1)

Sources & evidence

ORD record
ord-a1e00ca10ad54b588b23d5203394d289
Source dataset
uspto-grants-2003_09
Patent number
US06613876B1

Reaction notes

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