Diisopropylethylamine → (1R,2R)-N-(tert-butoxy)-1-fluoro-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamide

HRID 736815

反応式

HRID 736815 の反応式
[F:1][C@:2]1([C:30]([OH:32])=O)[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH3:29])[CH:20]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9].F[P-](F)(F)(F)(F)F.[N:40]1([O:49][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[C:61](NO)([CH3:64])([CH3:63])[CH3:62].C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[C:61]([O:49][NH:40][C:30]([C@@:2]1([F:1])[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([CH3:29])[CH:20]=2)=[CH:13][CH:12]=1)(=[O:9])=[O:10])=[O:32])([CH3:62])([CH3:63])[CH3:64]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2777896N-tert-butylhydroxylamine hydrochlorideHCID 68819242(1R,2R)-1-fluoro-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid

生成物 1

HCID 86607911(1R,2R)-N-(tert-butoxy)-1-fluoro-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamide収率 73.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 0.15 g (3 mmol) of (1R,2R)-1-fluoro-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid in DMF (4 mL) was added benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate (0.16 g, 1.2 eq), tert-butyl hydroxylamine hydrochloride (0.078 g, 2 eq) and diisopropylethylamine (0.22 mL, 4 eq). The resulting reaction mixture was stirred for 18 h, and then taken up in ethyl acetate, washed with brine, dried over Mg2SO4, filtered and concentrated. The residue was purified using silica chromatography, eluting with a gradient of 50-80% ethyl acetate/hexanes to afford (1R,2R)-N-(tert-butoxy)-1-fluoro-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamide (0.14 g, 60%, 2 steps). MS: 530.2 (M+H)+.

後処理

  1. customThe resulting reaction mixture
  2. washwashed with brine
  3. dry with materialdried over Mg2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. washeluting with a gradient of 50-80% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-9ae6c459ef584a0b92e88d69dd3f22a3
出典データセット
uspto-grants-2009_09
特許番号
US07595327B2

関連ノート

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