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

HRID 854657ノート

反応式

HRID 854657 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-b0eccd5725a74b22a96e0490508e88f6
出典データセット
uspto-grants-2007_08
特許番号
US07259177B2

反応ノート

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