Dichloromethane → tert-Butyl 4-[N-[2-Acetoxymethyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]amino]benzoate

HRID 47860

Reaction equation

HRID 47860 reaction equation
[C:1]([O:4][CH2:5][C:6]1[N:15]([CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:14](=[O:24])[C:13]2[C:8](=[CH:9][C:10]3[CH2:27][CH2:26][C:25](=O)[C:11]=3[CH:12]=2)[N:7]=1)(=[O:3])[CH3:2].ClCCl.[NH2:32][C:33]1[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:35][CH:34]=1.[B][B][B][B][B][B][B][B][B][B]>CO>[C:1]([O:4][CH2:5][C:6]1[N:15]([CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:14](=[O:24])[C:13]2[C:8](=[CH:9][C:10]3[CH2:27][CH2:26][CH:25]([NH:32][C:33]4[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])=[CH:35][CH:34]=4)[C:11]=3[CH:12]=2)[N:7]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 227442802-Acetoxymethyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4,6-dioneHCID 178419135HCID 178419135, compound

Product 1

HCID 22744292tert-Butyl 4-[N-[2-Acetoxymethyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]amino]benzoateYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Acetoxymethyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4,6-dione (0.140 g, 0.36 mmol) was suspended in anhydrous methanol (8 ml) and then anhydrous dichoromethane (4 ml) was added until a clear solution was obtained. Tert-butyl 4-aminobenzoate (0.084 g, 0.44 mmol) was then added followed by decaborane (0.014 g, 0.12 mmol). The reaction mixture was stirred overnight at room temperature under argon. The solvent was removed in vaciio, and the residue was purified by column chromatography on elution with 40% ethyl acetate in hexane. The product was obtained as a glass (0.127 g, 63%) 1H-NMR (CDCl3) 1.20 (s, 9H, POM C(CH3)3), 1.58 (s, 9H, CO2C(CH3)3), 2.20 (s, 3H, CH3CO), 2.02, 2.72 (2×m, 2H, 7-CH2), 3.13 (m, 2H, 8-CH2), 4.36 (d, J=7.7 Hz, 1H, NH), 5.15 (q, J=6.8 Hz, 1H, 6-H), 5.21 (s, 2H, 2-CH2), 6.12 (AB system, J=10.7 Hz, 2H, POM CH2), 6.67 (d, J=8.8 Hz, 2H, 3,5′-ArH), 7.57 (s, 1H, 9-H), 7.85 (d, J=8.9 Hz, 2H, 2′,6′-ArH), 8.25 (s, 1H, 5-H); MS (ESI, m/z) 564 (M+H)+.

Workup

  1. customwas obtained
  2. customThe solvent was removed in vaciio
  3. customthe residue was purified by column chromatography on elution with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f03d6aa238fc40688ad833f92817bec1
Source dataset
uspto-grants-2004_03
Patent number
US06699861B1

Linked notes

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