Trifluoroacetic acid → HCID 57979480、化合物

HRID 1867246ノート

反応式

HRID 1867246 の反応式
N[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](OC)=O)[C:3]=1[C:4]([OH:6])=O.[N+](C1C=CC=[C:20]([C:21](O)=[O:22])[C:19]=1C(O)=O)([O-])=O.C(O)(C(F)(F)F)=O>CO>[OH:6][CH2:4][C:3]1[CH:2]=[CH:10][CH:9]=[C:8]2[C:7]=1[CH:11]=[CH:19][CH:20]=[C:21]2[OH:22]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 690433-Nitrophthalic acidHCID 136599672-Amino-6-(methoxycarbonyl)benzoic acid

生成物 1

HCID 57979480HCID 57979480、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2-Amino-6-(methoxycarbonyl) benzoic acid (1) was made from 3-nitrophthalic acid using the procedure first reported by Rogers and Averill (Rodgers, M. E. and Averill, B. A., J. Org. Chem., 1986, 51, 3308) and then used immediately to make Diels Alder cycloadduct 2 via the 3-(methoxhycarbonyl)dehydrobenzene intermediate that is generated under aprotic diazotization reaction conditions (based on modified conditions first reported by Giles, R. G. F., Sargent, M. V., and Sianipar, H., J. Chem. Soc. Perkin Trans I, 1991, 1571). Treatment of cycloadduct 2 with TFA in refluxing methanol yielded a 1:2 mixture of regioisomeric naphthols 3a and 3b which were separated by column chromatography on silica gel. The 1,5-naphthol regioisomer (3a) was then reduced with LAH to produce 5-hydroxymethyl naphthol 4, which was then coupled to carbapenem intermediate 5 (CPI 5) with catalytic palladium to produce the 1-carbon naphthol coupled CPI 6.

後処理

  1. customthat is generated under aprotic diazotization reaction conditions (
  2. customyielded
  3. customwere separated by column chromatography on silica gel

出典と根拠

ORDレコード
ord-f6e39f17ecc54888833ea29b15f2d875
出典データセット
uspto-grants-2009_12
特許番号
US07632828B2

反応ノート

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