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 1094303노트

반응식

HRID 1094303 반응식
[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]

참가 물질

7

반응물 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

생성물 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-acetamide수율 18.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-84c70f2cc7054e1a9151fb168450957b
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133910B2

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