Dimethylformamide → cis-[2[[[[(1,1-Dimethylethoxy)carbonyl]amino]acetyl]amino]cyclohexyl]-carbamic acid benzyl ester

HRID 2101428Notes

Reaction equation

HRID 2101428 reaction equation
CN1[CH2:7][CH2:6][O:5]CC1.[NH:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C:10]([OH:12])=O.CN([P+](O[N:31]1N=[N:38][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN([CH:50]=[O:51])C>>[CH2:6]([O:5][C:50](=[O:51])[NH:38][C@@H:33]1[CH2:34][CH2:35][CH2:36][CH2:37][C@@H:32]1[NH:31][C:10](=[O:12])[CH2:9][NH:8][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:7]1[CH:36]=[CH:37][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 68827563cis-[2[[[[(1,1-Dimethylethoxy)carbonyl]amino]acetyl]amino]cyclohexyl]-carbamic acid benzyl ester

Conditions

Temperature
0 °C

Procedure

The material from above 1-(N-benzyloxycarbonyl)-cis-cyclohexane-1,2-diamine (5 g) was dissolved in DMF (100 mL). After cooling to 0° C., 4-methylmorpholine (11 mL) and N-Boc-Gly-OH (4.2 g) were added. BOP Reagent (11.6 g) was added, and the mixture was stirred at rt for 18 h. The DMF was removed. EtOAc was added along with 1 N HCl solution. The EtOAc layer was washed with 1 N HCl, NaHCO3 solution, and brine. The EtOAc was dried (MgSO4), filtered, and concentrated to give cis-[2[[[[(1,1-dimethylethoxy)carbonyl]amino]acetyl]amino]cyclohexyl]-carbamic acid benzyl ester (9.6 g). MS found: (M+H)+=406.3.

Workup

  1. customThe DMF was removed
  2. additionEtOAc was added along with 1 N HCl solution
  3. washThe EtOAc layer was washed with 1 N HCl, NaHCO3 solution, and brine
  4. dry with materialThe EtOAc was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-99fac8bcc6c54298a3ddfd7988bda566
Source dataset
uspto-grants-2009_08
Patent number
US07572813B2

Reaction notes

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