Benzaldehyde → 2-{Benzyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}acetic acid

HRID 854657Notes

Reaction equation

HRID 854657 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:14][O:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([CH2:22][NH:23][CH2:24][C:25]([O:27]C(C)C)=[O:26])[CH2:17]1.[CH:31](=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[O-]S([O-])(=O)=O.[Mg+2].[B-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl.O>[CH2:31]([N:23]([CH2:22][C@H:18]1[CH2:19][CH2:20][CH2:21][C@@H:16]([O:15][CH2:14][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])[CH2:17]1)[CH2:24][C:25]([OH:27])=[O:26])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 23676153Sodium bis(acetyloxy)boranuidyl acetateHCID 69243360Isopropyl 2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)-cyclohexylmethyl]amino}acetate

Product 1

HCID 692408832-{Benzyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}acetic acidYield 11.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

120 mg of isopropyl 2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)-cyclohexylmethyl]amino}acetate are dissolved in 1.5 ml of dichloromethane, and 62 mg of benzaldehyde, a spatula tip of MgSO4 and 68 mg of sodium triacetoxyborohyride are added successively. The suspension is stirred at RT overnight, and water is then added. The oraganic phase is separated off, washed with Na2CO3 solution, dried over MgSO4 and concentrated. The residue is dissolved in 0.7 ml of methanol and 0.23 ml of water, 20 mg of LiOH are added and the mixture is stirred at RT overnight. The solution is concentrated and the residue is purified by preparative HPLC, yielding 15 mg of 2-{benzyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}acetic acid. C28H34N2O4 (462.59); MS (ESI): 463 (MH+).

Workup

  1. customThe oraganic phase is separated off
  2. washwashed with Na2CO3 solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in 0.7 ml of methanol
  6. addition0.23 ml of water, 20 mg of LiOH are added
  7. stirringthe mixture is stirred at RT overnight
  8. concentrationThe solution is concentrated
  9. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-b0eccd5725a74b22a96e0490508e88f6
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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