HCID 73855545, compound → HCID 72395064, compound

HRID 2214595Notes

Reaction equation

HRID 2214595 reaction equation
C[C:2]1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:9])[C:4](=[O:24])[O:3]1>CO>[CH3:2][O:3][C:4](=[O:24])[C:5]([OH:6])=[CH:7][C:8](=[O:9])[N:10]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[O:11][CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

3

Reactant 1

HCID 73855545HCID 73855545, compound

Product 1

HCID 72395064HCID 72395064, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-(4-fluorobenzyl)-N-isobutoxy-acetamide was treated with methanol as described in the preparation of Compound 44-D and gave the title ester as white crystals (48% yield); mp 55–56° C. 1HNMR 400 MHz (CDCl3) δ (ppm): mixture of rotamers: 0.99 (6H, d, J=7.1 Hz, CH3), 1.96 (1H, m, CH), 3.65 (2H, d, J=6.0 Hz, OCH2), 3.91 (3H, s, OCH3), 4.81 (2H, s, NCH2), 6.49 (1H, s, CH), 7.05 (2H, m, aromatics), 7.33 (2H, m, aromatics), 13.4 (1H, broad s, OH). HRMS (ES+) calculated for C16H21FNO5, [M+H]+: 326.140376. found: 326.139560.

Workup

  1. customas described in the preparation of Compound 44-D

Sources & evidence

ORD record
ord-40cf5d2347a04ce5be5ca1263772cf7b
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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