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Diisopropylethylamine → (3R,4R)-4-(4-(Benzyloxy)phenylsulfonamido)-N-tert-butoxy-3-methyl-tetrahydro-2H-pyran-3-carboxamide

HRID 736785
ノート
印刷プレビュー

反応式

HRID 736785 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([CH3:28])[C:25](O)=[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.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.Cl.[C:66]([O:70][NH2:71])([CH3:69])([CH3:68])[CH3:67]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([NH:18][C@@H:19]2[CH2:24][CH2:23][O:22][CH2:21][C@:20]2([CH3:28])[C:25]([NH:71][O:70][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:26])(=[O:17])=[O:16])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 68819207(3R,4R)-4-(4-(benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylic acid

生成物 1

HCID 86607886(3R,4R)-4-(4-(Benzyloxy)phenylsulfonamido)-N-tert-butoxy-3-methyl-tetrahydro-2H-pyran-3-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(3R,4R)-4-(4-(Benzyloxy)phenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxylic acid (715 mg, 1.76 mmol) was dissolved in DMF (8 mL), and BOP reagent (1.01 g, 2.29 mmol, 1.3 eq), N,N-diisopropylethylamine (1.2 mL, 7.04 mmol, 4.0 eq) and O-(tert-butyl)hydroxylamine hydrochloride (332 mg, 2.64 mmol, 1.5 eq) were sequentially added. The reaction was stirred at room temperature overnight and then diluted with ethyl acetate (200 mL), and washed with water (3×50 mL). The aqueous layer was re-extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, and concentrated affording (3R,4R)-4-(4-(benzyloxy)phenylsulfonamido)-N-tert-butoxy-3-methyl-tetrahydro-2H-pyran-3-carboxamide as white fluffy powder that was used in the next step without purification. MS: (M+Na)+=499.0; (M−H)−=475.2.

後処理

  1. washwashed with water (3×50 mL)
  2. extractionThe aqueous layer was re-extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-94726e1948fb4b179635004d2aaae05a
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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