Trifluoroacetic acid → HCID 57979480, compound

HRID 1867246Notes

Reaction equation

HRID 1867246 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 57979480HCID 57979480, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-f6e39f17ecc54888833ea29b15f2d875
Source dataset
uspto-grants-2009_12
Patent number
US07632828B2

Reaction notes

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