Ethyl Acetate → HCID 86652468, compound

HRID 1876300Notes

Reaction equation

HRID 1876300 reaction equation
[CH3:1][C@@H:2]1[C@H:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])(C)C)[CH2:6][CH2:5][C:4](=[O:16])[O:3]1.[CH3:17][CH2:18]OC(C)=O>C(Cl)(Cl)Cl>[CH3:1][C@@H:2]1[C@H:7]([NH:8][C:9](=[O:15])[O:10][CH2:11][CH2:14][CH2:17][CH3:18])[CH2:6][CH2:5][C:4](=[O:16])[O:3]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 10933254HCID 10933254, compound

Product 1

HCID 86652468HCID 86652468, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Data for tert-butyl (2R,3R)-2-methyl-6-oxo-tetrahydro-2H-pyran-3-ylcarbamate: m.p.=98.2-99.5° C.; Rf=0.27 (50% EtOAc in hexanes); IR (neat): 3337, 2979, 2935, 1709 (C═O), 1697 (C═O), 1527, 1250, 1171, 1059 cm−1; [α]D25+38.8 (c 1.0, CHCl3); 1H NMR (300 MHz, 293 K, CDCl3) δ 4.74 (br, 1H), 4.52 (ddd, 1H, J=12.9, 6.3, 2.4 Hz), 3.99 (m br, 1H), 2.55 (dd, 2H, J=8.1, 6.9 Hz), 2.24-2.12 (m, 1H), 1.99-1.88 (m, 1H), 1.43 (s, 9H), 1.33 (d, 3H, J=6.6 Hz); 13C NMR (75 MHz, 293K, CDCl3) δ 171.2, 155.5, 79.8, 77.4, 46.6, 28.2, 26.0, 25.5, 16.8; HRMS (EI+) calcd. for C11H19NO4 (M)+ 229.1314. found 229.1306.

Sources & evidence

ORD record
ord-e9547040252144d7901887917f6fb8b3
Source dataset
uspto-grants-2012_11
Patent number
US08309599B2

Reaction notes

Loading…