HCID 23519155, compound → HCID 74058496, compound

HRID 1836536Notes

Reaction equation

[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8](Cl)=[O:9])[C:4](=[O:11])[O:3]1.[C:13]([O:17][C:18](=[O:29])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26][O:27][CH3:28])=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18](=[O:29])[C:19]1[CH:20]=[CH:21][C:22]([CH2:25][N:26]([C:8](=[O:9])[CH:7]=[C:5]2[C:4](=[O:11])[O:3][C:2]([CH3:12])([CH3:1])[O:6]2)[O:27][CH3:28])=[CH:23][CH:24]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

Reactant 2

HCID 23519155HCID 23519155, compound

HCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 74058496HCID 74058496, compoundYield 93%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride with 4-(methoxyamino-methyl)-benzoic acid tert-butyl ester as described in the preparation of compound 1-A gave the title amide as white crystals (93% yield): mp 137-138° C. (dichloromethane-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.58 (9H, s, t-Bu), 1.76 (6H, s, CH3), 3.67 (3H, s, OCH3), 4.87 (2H, s, NCH2), 6.40 (1H, s, CH), 7.39 (2H, d, J=8.2 Hz, aromatics), 7.95 (2H, d, J=8.2 Hz, aromatics). Anal. calcd for C20H25NO7: C, 61.37; H. 6.44; N, 3.58. Found: C, 61.23; H, 6.25; N, 3.52.

Sources & evidence

ORD record: ord-6580183e378e4315b082e756e242ebb0
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777440B2

Reaction notes

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