Ethyl bromoacetate → HCID 14468444, compound
Reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)([OH:3])=[O:2].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>>[CH2:19]([O:18][C:16]([CH2:15][O:2][C:1]([C:4]1[O:5][C:6]2[C:12]([O:13][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)=[O:3])=[O:17])[CH3:20]Participants
Procedure
2-Carboxy-7-hydroxybenzofuran and ethyl bromoacetate were reacted to give 2-(ethoxycarbonylmethoxycarbonyl)-7-(ethoxycarbonylmethoxy)benzofuran (yield: 78%, MS (m/z): 350 (M+), 305, 277, 249 and 219), which was then reacted with chlorosulfonic acid as in Example 1, yielding 2-(ethoxycarbonylmethoxycarbonyl)-4-chlorosulfonyl-7-ethoxycarbonylmethoxybenzofuran (yield: 68%, MS (m/z): 448 (M+), 413, 382 and 350). The obtained chlorosulfonyl compound was reacted with glycine ethyl ester hydrochloride as in Example 1 to give an ester compound (yield: 98%, MS (m/z): 515 (M+), 470, 442, 414 and 350), which was then hydrolyzed to give 2-carboxy-4-(N-carboxy-methylsulfamoyl)-7-(carboxymethoxy)benzofuran (colorless needles, yield: 83%). The physical constants are shown in Table 4.
Sources & evidence
- ORD record
- ord-34969112b6d14d0f9bc6c33c8d9ebbdc
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04666931
Reaction notes
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