1-Heptanamine → 4-{[(Heptylcarbamoyl)oxy]methyl}-2-methoxyphenyl acetate

HRID 1798413Notes

Reaction equation

HRID 1798413 reaction equation
S=C1[N:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18](=[O:20])[CH3:19])=[C:13]([O:21][CH3:22])[CH:12]=2)=[O:8])[CH2:5][CH2:4]S1.[CH2:23](N)[CH2:24][CH2:25][CH2:26][CH2:27]CC.C(N(CC)CC)C>ClCCl>[C:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][O:9][C:7](=[O:8])[NH:6][CH2:5][CH2:4][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:12][C:13]=1[O:21][CH3:22])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 81271-HeptanamineHCID 8471TriethylamineHCID 568478684-(Acetyloxy)-3-methoxybenzyl 2-thioxo-1,3-thiazolidine-3-carboxylate

Product 1

HCID 568478704-{[(Heptylcarbamoyl)oxy]methyl}-2-methoxyphenyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A yellow solution of VII (87 mg, 0.255 mmol), n-heptylamine (31 mg, 1.05×0.255 mmol) and triethylamine (26 mg, 36 μL, 0.255 mmol) in 3 mL of dichloromethane was stirred at room temperature overnight. The reaction was worked up as described for 7. The product was purified by preparative thick layer chromatography using dichloromethane/diisopropyl ether, 9:1, v/v, as the developing solvent. The result was 58 mg (67%) of 6 as a clear oil: Rf=0.53 (dichloromethane/acetone, 97:3, v/v); 1HNMR (CDCl3) δ 6.98 (d, 3J=8.0 Hz, 1H), 6.94 (s, 1H), 6.91 (d, 3J=8.0 Hz, 1H), 4.98 (s, 2H), 4.73 (bs 1H, NH), 3.81 (s, 3H), 3.18-3.14 (m, 2H), 2.29 (s, 3H), 1.50-1.43 (m, 2H), 1.31-1.19 (m, 8H) and 0.85 (t, 3J=7.0 Hz, 3H). Exact mass (FAB+) calculated for C18H27NO5 [M+] 337.1889. found 337.1895.

Workup

  1. customThe product was purified by preparative thick layer chromatography

Sources & evidence

ORD record
ord-d3fd91c90330484faf83962b63ac49bb
Source dataset
uspto-grants-2013_01
Patent number
US08343971B2

Reaction notes

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