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Hydrochloric Acid → (3R,4R)-4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylic acid

HRID 736784
ノート
印刷プレビュー

反応式

HRID 736784 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@@H:19]2[CH2:24][CH2:23][O:22][CH2:21][C@:20]2([CH3:29])[C:25]([O:27]C)=[O:26])(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@@H:19]2[CH2:24][CH2:23][O:22][CH2:21][C@:20]2([CH3:29])[C:25]([OH:27])=[O:26])(=[O:16])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件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 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68818813(3R,4R)-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylate

生成物 1

HCID 68819207(3R,4R)-4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylic acid収率 88%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

(3R,4R)-Methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylate (856 mg, 2.04 mmol) was stirred with 15% NaOH (5 mL) in THF (5 mL) and MeOH (5 mL) at 45° C. overnight. The mixture was then cooled to 0° C. and acidified with 2N HCl to pH ˜3. After extraction with ethyl acetate the organics were washed with brine, dried over MgSO4, and concentrated. The residue was triturated with ether to yield 726 mg (88%) of (3R,4R)-4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylic acid as a white solid. MS: (M+Na)+=428.0; (M−H)−=404.1.

後処理

  1. extractionAfter extraction with ethyl acetate the
  2. washorganics were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-bc3f706328504a67ae19cbf9e9b78d93
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

読み込み中…

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