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Sodium Bicarbonate → (3R,4R)-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylate

HRID 736783
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HRID 736783 반응식
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][C:4]1([CH3:13])[C:9]([O:11][CH3:12])=[O:10].[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:2][C@@H:3]2[CH2:8][CH2:7][O:6][CH2:5][C@:4]2([CH3:13])[C:9]([O:11][CH3:12])=[O:10])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:2][C@@H:3]2[CH2:8][CH2:7][O:6][CH2:5][C@@:4]2([CH3:13])[C:9]([O:11][CH3:12])=[O:10])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 47383854-(Benzyloxy)benzene-1-sulfonyl chlorideHCID 68817485Methyl 4-amino-3-methyloxane-3-carboxylate hydrochloride

생성물 2

HCID 68818813(3R,4R)-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylateHCID 68819217(3S,4R)-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Crude methyl 4-amino-3-methyl-tetrahydro-2H-pyran-3-carboxylate hydrochloride (8.65 mmol), 4-benzyloxy-benzenesulfonyl chloride (1.2 eq), CH2Cl2 (175 mL) and saturated NaHCO3 (90 mL) were combined and stirred at room temperature overnight. The organic phase was then washed with water (100 mL) and brine (100 mL), dried over MgSO4, and concentrated. The residue was purified by chromatography with 20-35% ethyl acetate/hexane to provide two diastereomers, (3R,4R)-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylate and (3S,4R)-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylate. MS: (M+H)+=420.0.

후처리

  1. washThe organic phase was then washed with water (100 mL) and brine (100 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography with 20-35% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-97dd439fff3d4c14ba25174825765800
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07595327B2

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