Propionyl chloride → N-[(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl]-propionamide

HRID 215848노트

반응식

HRID 215848 반응식
FC(F)(F)C(O)=O.[NH2:8][C@H:9]1[CH2:13][C@@H:12]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([Cl:38])=[N:18][C:19]=3[NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:11]([OH:39])[C@@H:10]1[OH:40].CCN(C(C)C)C(C)C.[C:50](Cl)(=[O:53])[CH2:51][CH3:52]>C1COCC1>[Cl:38][C:17]1[N:16]=[C:15]2[C:20]([N:21]=[CH:22][N:14]2[C@@H:12]2[CH2:13][C@H:9]([NH:8][C:50](=[O:53])[CH2:51][CH3:52])[C@@H:10]([OH:40])[C@H:11]2[OH:39])=[C:19]([NH:23][CH2:24][CH:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:18]=1

참가 물질

5

반응물 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 86622631(1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol trifluoroacetate

생성물 1

HCID 86622630N-[(1S,2R,3S,4R)-4-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl]-propionamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(1S,2R,3S,5R)-3-Amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol trifluoroacetate (9.50 g, 16.42 mmol) and DIPEA (6.36 g, 49.27 mmol) are placed in a flask with dry THF (150 mL). Propionyl chloride (1.52 g, 16.42 mmol) is added dropwise and the reaction mixture is stirred at RT. The reaction is shown to be complete by LCMS after 1 hour. The solvent is removed in vacuo and the residue is partitioned between DCM (250 mL) and water (250 mL). The organic layer is washed with water (200 mL) and brine (200 mL), dried over MgSO4, filtered and the solvent is removed in vacuo. The solid is re-crystallised from 1,2-dichloroethane to give the title compound.

후처리

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between DCM (250 mL) and water (250 mL)
  3. washThe organic layer is washed with water (200 mL) and brine (200 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe solid is re-crystallised from 1,2-dichloroethane

출처 및 근거

ORD 기록
ord-7d35a1afd8404194bbee1aa909948dd8
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193164B2

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