1,2-Dichloroethane → tert-Butyl 5-carbamoylisoindoline-2-carboxylate

HRID 268712ノート

反応式

HRID 268712 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([OH:19])=O)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=[N:30]C=2C=1.N>CN(C=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([NH2:30])=[O:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 164501432-(tert-Butoxycarbonyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid

生成物 1

HCID 68966998tert-Butyl 5-carbamoylisoindoline-2-carboxylate収率 64.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

A mixture of N-t-butoxycarbonyl-5-carboxyisoindoline (D13) (240 mg), EDC (350 mg), HOBT (140 mg), triethylamine (0.32 ml) and 0.880 ammonia solution (1 ml) in DMF (10 ml) was stirred overnight at rt and then evaporated. The residue was partitioned between EtOAc (10 ml) and 5% citric acid (10 ml). The organic layer was collected, washed with water (10 ml), saturated NaHCO3 solution (10 ml), water (10 ml), brine (10 ml), dried (MgSO4) and evaporated to give the title compound (D14) (154 mg). MS electrospray (+ion) 263 (MH+). 1H NMR δ (CDCl3), 7.73 (2H, m), 7.26 (1H, m), 6.88 (2H, m), 4.72 (2H, s), 4.69 (2H, s),1.52 (9H, s).

後処理

  1. customevaporated
  2. customThe residue was partitioned between EtOAc (10 ml) and 5% citric acid (10 ml)
  3. customThe organic layer was collected
  4. washwashed with water (10 ml), saturated NaHCO3 solution (10 ml), water (10 ml), brine (10 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

出典と根拠

ORDレコード
ord-50a7436659874062881878ed88391b53
出典データセット
uspto-grants-2008_11
特許番号
US07446103B2

反応ノート

読み込み中…