Trifluoroacetic acid → HCID 57979480, 화합물

HRID 1867246노트

반응식

HRID 1867246 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 57979480HCID 57979480, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f6e39f17ecc54888833ea29b15f2d875
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632828B2

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