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

HRID 268712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 268712
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 68966998tert-Butyl 5-carbamoylisoindoline-2-carboxylateAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-50a7436659874062881878ed88391b53
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446103B2

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