Carbon Dioxide → HCID 19029178, compound

HRID 2256010Notes

Reaction equation

HRID 2256010 reaction equation
C(=O)=O.[C:4]([NH:7][CH:8]([C:12]1([CH3:17])[CH2:16][CH:15]=[CH:14][O:13]1)[C:9]([OH:11])=O)(=[O:6])[CH3:5].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[C:4]([NH:7][CH:8]([C:12]1([CH3:17])[CH2:16][CH:15]=[CH:14][O:13]1)[C:9]([NH:40][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:11])(=[O:6])[CH3:5]

Participants

6

Reactant 5

HCID 280Carbon DioxideHCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 19029198HCID 19029198, compound

Product 1

HCID 19029178HCID 19029178, compoundYield 43%

Procedure

Employing the mixed carbonic anhydride coupling procedure with 18 (2.40 g, 12.2 mmol), 4-methylmorpholine (1.23 g, 12.2 mmol), isobutylchloroformate (1.83 g, 13.4 mmol), and benzylamine (1.43 g, 12.7 mmol) gave 4 (1.50 g, 43%) as a thick oil: Rf 0.29 (2% MeOH/CHCl3); 1H NMR (CDCl3) δ 1.94 (s, CH3), 1.98 (s, C(O)CH3), 4.40 (d, J=5.6 Hz, CH2), 6.20 (br s, NH), 6.34-6.37 (m, C3H, C4H), 7.05-7.36 (m, NH, C5H, 5 PhH); 13C NMR (CDCl3) 22.31 (C(O)CH3), 23.81 (CH3), 43.77 (CH2), 58.50 (C(CH3)), 107.94 (C4), 110.67 (C3), 126.99 (2C2 ' or 2C3 '), 127.41 (C4 '), 128.60 (2C2 ' or 2C3 '), 137.52 (C1 '), 142.38 (C5), 152.94 (C2), 169.03 (C(O)NH), 171.16 (COCH3) ppm; mass spectrum, m/e (relative intensity) 287 (M+ +1, 4), 228 (4), 153 (99), 152 (96), 138 (15), 111 (63), 110 (100), 91 (75); Mr (EI) 286.13074 (calcd for C16H18N2O3, 286.13174).

Sources & evidence

ORD record
ord-ffcc4b7f4b3e44f5ae5865df6c14be6c
Source dataset
uspto-grants-1997_08
Patent number
US05654301

Reaction notes

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