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

HRID 736783
ノート
印刷プレビュー

反応式

HRID 736783 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-97dd439fff3d4c14ba25174825765800
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07595327B2

反応ノート

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