Triethylamine → Ethyl 5-(((tert-butoxycarbonyl)amino)methyl)-1,3,4-oxadiazole-2-carboxylate

HRID 966422Notes

Reaction equation

HRID 966422 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][NH:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[O:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][N:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 10108216Ethyl (N-{2-[(tert-butoxy)carbonylamino]acetylamino}carbamoyl)formate

Product 1

HCID 10084542Ethyl 5-(((tert-butoxycarbonyl)amino)methyl)-1,3,4-oxadiazole-2-carboxylateYield 44.2%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of compound 7 (59 g, 200 mmol) and triethylamine (42 ml, 0.57 mol) in carbon tetrachloride (60 ml) is added to a stirred, room temperature of triphenylphosphine (63 g, 0.24 mol) in methylene chloride (900 ml). The reaction mixture is stirred for 30 minutes and then refluxed for 12 hours. After cooling to room temperature, the volatiles are removed in vacuo and the resulting residue is filtered through silica using methylene chloride:ethyl acetate (9:1) as the eluent. After removing the volatiles in vacuo, the crude product is purified by flash column chromatography over silica gel using methylene chloride:ethyl acetate (19:1) as the eluent. 24 g (44%) Of compound 8 is obtained as orange oil, which solidifies to a yellow solid on standing.

Workup

  1. temperaturerefluxed for 12 hours
  2. customthe volatiles are removed in vacuo
  3. filtrationthe resulting residue is filtered through silica
  4. customAfter removing the volatiles in vacuo
  5. customthe crude product is purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-45471497c03e4d5e9a4605d130436714
Source dataset
uspto-grants-2005_10
Patent number
US06951946B2

Reaction notes

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