Formic Acid → HCID 22105511, compound

HRID 1455986Notes

Reaction equation

HRID 1455986 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH2:19][C:20]2[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)C(OC(C)(C)C)=O)=[N:9][CH:10]=1)=[O:4].C(O)=O>C(OCC)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][CH2:19][C:20]2[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 22105570HCID 22105570, compound

Product 1

HCID 22105511HCID 22105511, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl-2-[N-(2-benzyloxy-5-nitrobenzyl)-N-t-butoxycarbonylamino]pyridine-5-carboxylate (5.2 g) and formic acid (20 ml) was heated on a steam bath to give a clear solution. The mixture was evaporated to dryness and the residue obtained was dissolved in diethylether (100 ml) and washed with saturated sodium bicarbonate. The organic layer was dried and evaporated to give methyl-2-[N-(2-benzyloxy-5-nitrobenzyl)-amino]pyridine-5-carboxylate, yield 3.3 g. This same procedure was used to prepare ethyl-2-[N-(2-benzyloxy-5-bromobenzyl)-amino]thiophene-5-carboxylate.

Workup

  1. temperaturewas heated on a steam bath
  2. customto give a clear solution
  3. customThe mixture was evaporated to dryness
  4. customthe residue obtained
  5. washwashed with saturated sodium bicarbonate
  6. customThe organic layer was dried
  7. customevaporated

Sources & evidence

ORD record
ord-b3616f35a2ca497c9b1c0527ba87aa55
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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