Methyl chloroformate → HCID 22961820, compound

HRID 365878Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([O:10][CH2:11][C@@H:12]2[CH2:15][CH2:14][N:13]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=[N:7][C:8]=1Cl.Cl[C:24]([O:26][CH3:27])=[O:25].C(Cl)(=O)C1C=CC=CC=1>>[C:16]([N:13]1[CH2:14][CH2:15][C@H:12]1[CH2:11][O:10][C:5]1[CH:6]=[N:7][CH:8]=[C:3]([CH2:2][NH:1][C:24]([O:26][CH3:27])=[O:25])[CH:4]=1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

Reactant 3

HCID 6586Methyl chloroformate

HCID 7412Benzoyl chloride

HCID 22872662HCID 22872662, compound

Product 1

HCID 22961820HCID 22961820, compoundYield 94%

Procedure

Following the general procedure of Example 92c, substituting 5-aminomethyl-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from Example 205b for 5-aminomethyl-3-(1-BOC-2-(S)-azetidinylmethoxy)-6-chloropyridine and methyl chloroformate for benzoyl chloride therein, the title compound (0.23 g, 94%) was prepared: 1H NMR (CDCl3, 300 MHz) δ1.42 (s, 9H), 2.20-2.41 (m, 2H), 3.72 (s, 3H), 3.87 (t, J=7.5 Hz, 2H), 4.15 (dd, J=2.5, 10.0 Hz, 1H), 4.33-4.39 (m, 3H), 4.55 (m, 1H), 7.10 (s, 1H), 8.17 (s, 1H), 8.27 (d, J=1.5 Hz, 1H); MS (CI/NH3) m/z 352 (M+H)+.

Sources & evidence

ORD record: ord-62c4118e166d42cc8ed65948f8f20c18
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127386

Reaction notes

Loading…