Methyl 3-(chloromethyl)benzoate → HCID 57214068, compound

HRID 1459628Notes

Reaction equation

HRID 1459628 reaction equation
[O:1]([CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.[CH3:22][O:23][C:24]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Cl)=[O:25]>>[OH:1][CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[N:15]([CH2:29][C:28]2[CH:27]=[C:26]([CH:33]=[CH:32][CH:31]=2)[C:24]([O:23][CH3:22])=[O:25])[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1

Participants

3

Reactant 2

HCID 3248988Methyl 3-(chloromethyl)benzoateHCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 57214068HCID 57214068, compoundYield 87%

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by methods F and G, alkylating with 3-(methoxycarbonyl)benzyl chloride, and isolated as a white powder in 87% yield, mp 73°-75° C.; 1H NMR (CDCl3) δ 7.92-7.95 (m, 2H), 7.38-7.43 (m, 2H), 6.96-7.03 (m, 2H), 6.91 (dt, J=2.3, 7.3 Hz, 1H), 6.81 (dd, J=1.4, 7.7 Hz, 1H), 5.23 (d, J=16.3 Hz, 1H), 5.16 (d, J=16.3 Hz, 1H), 4.87 (dd, J=5.7, 7.4 Hz, 1H), 3.92-3.95 (m, 2H), 3.91 (s, 3H), 2.21-2.37 (m, 3H containing one exchangeable hydrogen). 13C NMR (CDCl3) δ 166.9, 166.7, 144.2, 136.5, 130.9 (CH), 130.7, 129.1 (CH), 128.7 (CH), 128.5, 127.7 (CH), 124.3 (CH), 122.9 (CH), 117.4 (CH), 115.4 (CH), 75.3 (CH), 58.9 (CH2), 52.2 (CH2), 45.1 (CH2), 33.3 (CH2). IR 3569, 2948, 1709, 1676, 1502 cm-1. MS 342 (MH+). Anal. Calc'd. for C19H19NO5 : C, 66.85; H, 5.61; N, 4.10. Found: C, 66.37; H, 5.62; N, 3.97.

Workup

  1. customisolated as a white powder in 87% yield, mp 73°-75° C.

Sources & evidence

ORD record
ord-4094c296b3ea457fad41fcb2dae94eaa
Source dataset
uspto-grants-1998_12
Patent number
US05854242

Reaction notes

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