Dimethylformamide → tert-Butyl carbamate

HRID 745130Notes

Reaction equation

HRID 745130 reaction equation
C(O)(=O)[C@@H:2]([C:4]1[CH:9]=CC=C[CH:5]=1)[OH:3].C[N:13]([P+]([O:22]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.C[N:47]([CH:49]=[O:50])C>>[NH4+:13].[OH-:3].[C:49](=[O:50])([O:22][C:4]([CH3:2])([CH3:5])[CH3:9])[NH2:47]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 11914(-)-Mandelic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 2

HCID 14923Ammonium HydroxideHCID 77922tert-Butyl carbamateYield 72%

Procedure

To a solution of (R)-mandelic acid (100 mg, 0,225 mmol) in DMF (0.5 mL) was added Compound 54 (37.6 mg, 0.247 mmol), followed by BOP reagent (241 mg, 0.545 mmol) and N-methylmorpholine (132 μL, 1.20 mmol) at 0° C. The mixture was stirred at RT for 16 h. DMF was removed in vacuo and the residue dissolved in EtOAC, washed with saturated aq. NaHCO3 and then with brine. The organic layer was separated, dried (MgSO4) and concentrated in vacuo and the residue purified by silica gel chromatography, eluting with 99:1:0.1 to 91.5:8.5:0.85 CH2Cl2 :CH3OH:aq. NH4OH to afford Compound 377 (94 mg, 72%) as a white solid.

Workup

  1. customDMF was removed in vacuo
  2. dissolutionthe residue dissolved in EtOAC
  3. washwashed with saturated aq. NaHCO3
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe residue purified by silica gel chromatography
  8. washeluting with 99:1:0.1 to 91.5:8.5:0.85 CH2Cl2

Sources & evidence

ORD record
ord-bbbfcd3c8ad74f9e90a1f68c8903192e
Source dataset
uspto-grants-1996_09
Patent number
US05559256

Reaction notes

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