tert-Butyl carbazate → HCID 60066063、化合物

HRID 2306612ノート

反応式

HRID 2306612 の反応式
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]

参加物

6

反応物 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

生成物 1

HCID 60066063HCID 60066063、化合物収率 100.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0b59fe9317bc470ab058badb5d519387
出典データセット
uspto-grants-2004_12
特許番号
US06828317B2

反応ノート

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