Glycolic Acid → HCID 24853450、化合物

HRID 2065917ノート

反応式

HRID 2065917 の反応式
[NH2:1][CH2:2][CH:3]([OH:30])[CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[N:17]=[C:16]([C:18]3[CH:19]=[N:20][C:21]([CH2:26][CH3:27])=[C:22]([CH2:24][CH3:25])[CH:23]=3)[O:15][N:14]=2)=[CH:8][C:7]=1[CH2:28][CH3:29].[C:31](O)(=[O:34])[CH2:32][OH:33].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CC(=O)OCC>[CH2:24]([C:22]1[CH:23]=[C:18]([C:16]2[O:15][N:14]=[C:13]([C:9]3[CH:10]=[C:11]([CH3:12])[C:6]([O:5][CH2:4][CH:3]([OH:30])[CH2:2][NH:1][C:32](=[O:33])[CH2:31][OH:34])=[C:7]([CH2:28][CH3:29])[CH:8]=3)[N:17]=2)[CH:19]=[N:20][C:21]=1[CH2:26][CH3:27])[CH3:25]

参加物

7

反応物 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59392500HCID 59392500、化合物

生成物 1

HCID 24853450HCID 24853450、化合物収率 80%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (RS)-1-amino-3-{4-[5-(5,6-diethyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propan-2-ol (99 mg, 0.24 mmol), glycolic acid (18.5 mg, 0.244 mmol) and Hünig's base (78 mg, 0.61 mmol) in DCM (5 mL) is added PyBOP (126.7 mg, 0.24 mmol) and the mixture is stirred at rt for 30 min. The mixture is diluted with EA, washed with sat. aq. NaHCO3 solution, dried over MgSO4, filtered and concentrated. The crude product is purified by chromatography on prep. TLC plates eluting with DCM:MeOH 10:1 to give N—((RS)-3-{4-[5-(5,6-diethyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide (90 mg) as an oil; LC-MS: tR=0.88 min, [M+1]+=469.25.

後処理

  1. washwashed with sat. aq. NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by chromatography on prep
  6. washTLC plates eluting with DCM:MeOH 10:1

出典と根拠

ORDレコード
ord-f5967a2074ae494eba2e79065fa833fd
出典データセット
uspto-grants-2012_10
特許番号
US08288554B2

反応ノート

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