Methanol → HCID 54127080, compound

HRID 1956712Notes

Reaction equation

HRID 1956712 reaction equation
C(OCC)(=O)C.CO.[Cl:9][C:10]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:11]=1[CH2:12][NH:13][C:14]1[C:15](=O)[C:16](=[O:21])[C:17]=1[O:18]CC.[NH2:29][C@@H:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH3:31]>ClCCl.CCCCCC.C(O)C>[Cl:9][C:10]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:11]=1[CH2:12][NH:13][C:14]1[C:17](=[O:18])[C:16](=[O:21])[C:15]=1[NH:29][CH:30]([CH3:31])[C:32]([CH3:35])([CH3:34])[CH3:33]

Participants

8

Reactant 4

HCID 887MethanolHCID 8857Ethyl Acetate2×HCID 5324845(R)-3,3-Dimethyl-2-aminobutaneHCID 17819335HCID 17819335, compound

Product 1

HCID 54127080HCID 54127080, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

This compound was prepared according to the procedure described in Example 33. From 2-chloro-4,6-dimethylbenzaldehyde oxime (6.63 g, 36 mmol), zinc powder (9.4 g, 144 mmol), glacial acetic acid (72 mL), and 3,4-diethoxy-3-cyclobutene-1,2-dione (5.3 mL, 36 mmol) in absolute ethanol (180 mL) there was obtained after chromatography on silica gel (hexane:ethyl acetate, then 5% methanol in dichloromethane) followed by trituation with 10% ethyl acetate in hexane 5.32 g (50 %) of a solid. From a portion of this solid, 3-(2-chloro-4,6-dimethyl-benzylamino)-4-ethoxy-cyclobut-3-ene-1,2-dione, (0.4 g, 1.36 mmol) and (R)-2-amino-3,3-dimethylbutane (8.2 mL of a 0.2M solution in absolute ethanol, 1.64 mmol) and dichloromethane (3 mL). there was obtained after 4 days at room temperature a solid, which was filtered, rinsed with ethyl acetate, and dried. This gave 0.36 g (76%) of the (R) isomer of the title compound as a white solid: mp >300° C.; 1 H NMR (DMSO-d6) δ7.26 (br s, 1H), 7.19 (s, 1H), 7.14 (br d, 1H), 7.05 (s, 1H), 4.88 (d, 2H), 3.90 (m, 1H), 2.35 (s, 3H), 2.26 (s, 3H), 1.08 (d, 3H), 0.84 (s, 9H) ppm. IR (KBr): 3170, 2970, 1800, 1650 cm-1 ; MS (m/z) 348/350 (M+).

Workup

  1. customthere was obtained after 4 days at room temperature a solid, which
  2. filtrationwas filtered
  3. washrinsed with ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-a1a73ebdfe50424eb3fdbaf51b6de12c
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

Loading…