Ammonium Bicarbonate → HCID 86627962, compound

HRID 251738Notes

Reaction equation

HRID 251738 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH3:20])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.C(=O)(O)[O-].[NH4+:41]>O1CCOCC1>[NH2:41][C:10]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH3:20])=[O:11]

Participants

5

Reactant 3

HCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 11197378HCID 11197378, compound

Product 1

HCID 86627962HCID 86627962, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-8-oxodecanoic acid in dioxane were added Py (1 eq.), Boc2O (1.3 eq) and ammonium bicarbonate (1.26 eq.). The reaction mixture was stirred at RT for 72 hours and then the solvent was evaporated under reduced pressure. The resulting crude was diluted with EtOAc and washed with H2O, 1 N HCl and brine. The organic phase was dried (Na2SO4) and concentrated under reduced pressure to yield a white powder which was as such in the next step. MS (ES) C15H28N2O4 requires: 300, found: 301 (M+H+).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe resulting crude was diluted with EtOAc
  3. washwashed with H2O, 1 N HCl and brine
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto yield a white powder which

Sources & evidence

ORD record
ord-3593c156b27a4006884596e361a8a323
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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