Dicyclohexylcarbodiimide → HCID 70182183, compound

HRID 1898978Notes

Reaction equation

HRID 1898978 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:13]1[CH:18]=[C:17]2N=NN(O)[C:16]2=[CH:15][CH:14]=1.O.[CH2:24]1CCC(N=C=NC2CCCCC2)CC1.C([O:46][CH2:47][CH2:48][NH2:49])C1C=CC=CC=1>CCOC(C)=O>[C:1]([N:8]([CH2:9][CH2:10][O:12][CH2:24][C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:18]=1)[C:47](=[O:46])[CH2:48][NH2:49])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 5338682-(Benzyloxy)ethanamineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 70182183HCID 70182183, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of BOC-glycine (0.47 g, 2.69 mmol) in EtOAc (10 mL) was added HOBT hydrate (0.49 g, 3.22 mmol) followed by DCC (0.66 g, 3.22 mmol). After 30 minutes, a solution of benzyloxyethylamine (0.41 g, 2.69 mmol) in EtOAc (5 mL) was added and the mixture was stirred overnight at room temperature. The mixture was filtered, and the filtrate was diluted with EtOAc, washed with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated. Flash chromatography (EtOAc) gave 0.72 g (87%) of the title compound as a light yellow oil which slowly solidified; CI-MS 309 (m+1).

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with EtOAc
  3. washwashed with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-21d848fa10f64e9eb66f49e2f3b73b0c
Source dataset
uspto-grants-1996_11
Patent number
US05571792

Reaction notes

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