o-Phenylbenzoic acid → HCID 67018291, compound

HRID 1671674Notes

Reaction equation

HRID 1671674 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7]([OH:9])=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:58]([NH:65][CH2:66][CH:67]1[CH2:70][CH2:69][NH:68]1)([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59]>CN(C=O)C.CC(=O)OCC>[C:61]([O:60][C:58](=[O:59])[NH:65][CH2:66][CH:67]1[CH2:70][CH2:69][N:68]1[C:7]([C:2]1[C:1]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:9])([CH3:64])([CH3:62])[CH3:63]

Participants

7

Reactant 4

HCID 70357o-Phenylbenzoic acidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 14280902tert-Butyl [(azetidin-2-yl)methyl]carbamate

Product 1

HCID 67018291HCID 67018291, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 2-biphenylcarboxylic acid (107 mg), PyBOP (280 mg), DIEA (0.215 mL) in dry DMF (0.5 mL), was added a solution of 2-(N-Boc-aminomethyl)azetidine (100 mg) in dry DMF (0.5 mL). The resulting reaction mixture was stirred at RT for 20 h. The reaction mixture was diluted with EA, washed with water. The aqueous phase was extracted once again with EA, the combined organic extracts were dried (MgSO4), filtered and concentrated to yield the crude product as light brown oil. FC (EA) gave 140 mg (71%) of the title compound as a light yellow oil.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with water
  3. extractionThe aqueous phase was extracted once again with EA
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield the crude product as light brown oil

Sources & evidence

ORD record
ord-7b47be74a1934cefa39e9fa8bb592a8a
Source dataset
uspto-grants-2011_08
Patent number
US07994336B2

Reaction notes

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