Formic Acid → HCID 14987380, compound

HRID 2082374Notes

Reaction equation

HRID 2082374 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([O:24]C(C)(C)C)=[O:23])=[CH:12][CH:11]=2)[C:7]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:6][CH:5]=1)[CH2:2][CH3:3].C(O)=O>O>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([OH:24])=[O:23])=[CH:12][CH:11]=2)[C:7]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 14987379HCID 14987379, compound

Product 1

HCID 14987380HCID 14987380, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 5-n-propyl-1[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]pyrrole-2-carboxylate (600 mg, 1.34 mmol) was stirred with formic acid (6 ml) at room temperature for 4 hours (slowly dissolved to a homogeneous yellow solution). The mixture was diluted to about 50 ml with water to give a white precipitate which was filtered and subsequently purified by flash chromatography on silica gel (10% EtOAc/hexanes) to give 419 mg (80%) of the compound; m.p. 111°-115° C.

Workup

  1. dissolutionslowly dissolved to a homogeneous yellow solution)
  2. customto give a white precipitate which
  3. filtrationwas filtered
  4. customsubsequently purified by flash chromatography on silica gel (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d8180a4064b14c0f8751f3231b47eac9
Source dataset
uspto-grants-1993_02
Patent number
US05189048

Reaction notes

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