HCID 22905647, compound → HCID 22905656, compound

HRID 1488470Notes

Reaction equation

[C:1]([N:7]1[C:15]2[C:10](=[C:11]([CH3:22])[C:12]([O:18]C(=O)C)=[C:13]([CH3:17])[C:14]=2[CH3:16])[C:9]([CH3:24])([CH3:23])[CH2:8]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(N1C2C(=C(C)C(OC(=O)C)=C(C)C=2C)C(C)C1)(=O)C>>[C:1]([N:7]1[C:15]2[C:10](=[C:11]([CH3:22])[C:12]([OH:18])=[C:13]([CH3:17])[C:14]=2[CH3:16])[C:9]([CH3:24])([CH3:23])[CH2:8]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 22905647HCID 22905647, compound

HCID 22905661HCID 22905661, compound

Product 1

HCID 22905656HCID 22905656, compound

Procedure

Deacetylation of 31a was achieved as in the case of 29a. Product 31b was obtained as a white solid (79% yield), mp 164°-165° C. Spectral data: 1H NMR (CD3SOCD3): δ 1.25 (s, 6H), 1.90 (br s, 3H), 2.10 (s, 3H), 2.20 (s, 3H), 3.65 (br s, 2H), 7.85 (br s, 1H); 13C NMR (CD3SOCD3): δ 11.85, 12.75, 17.24, 23.41, 24.68, 42.57, 64.86, 117.90, 122.01, 124.93, 133.86, 137.71, 150.64, 168.32; CI-MS: m/z 248 (MH+, base), 230, 205, 190, 167; CI-HRMS (M+H+): Calcd. for C15H22NO2 248.1650, fnd. 248.1644. Anal: calcd. for C15H21NO2C, 72.7, H, 8.50, N, 5.70, fnd. C, 72.86, H, 8.46, N, 5.59.

Sources & evidence

ORD record: ord-b0940642b8054473a8c7672d363afc73
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05674876

Reaction notes

Loading…