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

HRID 1939382Notes

Reaction equation

HRID 1939382 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) δ7.92-7.95 (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) δ166.9, 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-d276fc00259c45f4b787460dd02af96c
Source dataset
uspto-grants-1997_12
Patent number
US05696117

Reaction notes

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