Glycolic Acid → N-(3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

HRID 1094303ノート

反応式

HRID 1094303 の反応式
[NH2:1][CH2:2][CH:3]([OH:26])[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[S:19][C:20]([CH2:23][CH3:24])=[CH:21][CH:22]=3)[O:15][N:14]=2)=[CH:8][C:7]=1[CH3:25].CCN(C(C)C)C(C)C.[C:36](O)(=[O:39])[CH2:37][OH:38].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl.CC(=O)OCC>[CH2:23]([C:20]1[S:19][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:26])[CH2:2][NH:1][C:37](=[O:38])[CH2:36][OH:39])=[C:7]([CH3:25])[CH:8]=3)[N:17]=2)=[CH:22][CH:21]=1)[CH3:24]

参加物

7

反応物 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 666369791-Amino-3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol

生成物 1

HCID 59202022N-(3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide収率 18.9%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a cold solution (0° C.) of 1-amino-3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (32 mg, 86 μmol) in DCM (1 mL), DIPEA (45 mg, 345 μmol), glycolic acid (13 mg, 172 μmol) and finally TBTU (33 mg, 101 μmol) is added. The mixture is stirred at rt for 1 h before it is diluted with EA and washed with water. The aq. phase is extracted back with EA. The combined org. extracts are dried over MgSO4, filtered and evaporated. The crude product is purified by crystallisation from acetonitrile to give N-(3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide (7 mg) as a white solid; LC-MS: tR=0.95 min, [M+1]+=432.16.

後処理

  1. washwashed with water
  2. extractionThe aq. phase is extracted back with EA
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by crystallisation from acetonitrile

出典と根拠

ORDレコード
ord-84c70f2cc7054e1a9151fb168450957b
出典データセット
uspto-grants-2012_03
特許番号
US08133910B2

反応ノート

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