tert-Butyl carbazate → HCID 60066063, compound

HRID 2306612Notes

Reaction equation

HRID 2306612 reaction equation
C(N(C(C)C)CC)(C)C.[N:10]([CH2:13][C@@H:14]1[O:18][C:17](=[O:19])[N:16]([C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[C:22]([F:29])[CH:21]=2)[CH2:15]1)=[N+:11]=[N-:12].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:54]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])(=[O:57])[NH:55][NH2:56]>CN(C=O)C>[C:59]([O:58][C:54]([NH:55][NH:56][C:24](=[O:26])[C:23]1[CH:27]=[CH:28][C:20]([N:16]2[CH2:15][C@H:14]([CH2:13][N:10]=[N+:11]=[N-:12])[O:18][C:17]2=[O:19])=[CH:21][C:22]=1[F:29])=[O:57])([CH3:62])([CH3:61])[CH3:60]

Participants

6

Reactant 4

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 129674524-[(5R)-5-(Azidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorobenzoic acid

Product 1

HCID 60066063HCID 60066063, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (4.67 ml, 0.0268 mol) is added to a mixture of 4-(5(R)-Azidomethyl-2-oxo-oxazolidin-3-yl)-2-fluorobenzoic acid (2.50 g, 0.00892 mol) [prepared according to the procedure described in U.S. Pat. No. 6,239,152] and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.73 g, 0.00981 mol) in DMF (30 ml) and stirred for 20 minutes at room temperature. tert-Butyl carbazate (1.30 g, 0.00981 mol) is then added and the mixture stirred at room temperature overnight. The reaction mixture is evaporated under vacuum and the residue diluted with water. The resulting precipitate is filtered and dried under vacuum to give product as a white solid (3.52 g, 99%); 1HNMR (300 MHz, DMSO-d6) δ 1.42 (s, 9H), 3.72-3.76 (m, 2H), 3.81 (dd, J=6.0, 9.3 Hz, 1H), 4.17 (t, J=9.1 Hz, 1H), 4.88-4.96 (m, 1H), 7.43 (dd, J=2.2, 8.8 Hz, 1H), 7.57 (dd, J=2.2, 13.2, 1H), 7.66 (t, J=8.2, 1H), 8.96 (s, 1H), 9.92 (s, 1H); Rf(EtOAc)=0.54; mp 173-5.

Workup

  1. customprepared
  2. customThe reaction mixture is evaporated under vacuum
  3. additionthe residue diluted with water
  4. filtrationThe resulting precipitate is filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0b59fe9317bc470ab058badb5d519387
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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