Glycolic Acid → HCID 24853450, 화합물

HRID 2065917노트

반응식

HRID 2065917 반응식
[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]

참가 물질

7

반응물 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59392500HCID 59392500, 화합물

생성물 1

HCID 24853450HCID 24853450, 화합물수율 80%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f5967a2074ae494eba2e79065fa833fd
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288554B2

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