Water → 4-Amino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-(2-oxo-2-(pyrrolidin-1-yl)ethyl)benzenesulfonamide

HRID 1256128ノート

反応式

HRID 1256128 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:6]([CH2:8][C:9](O)=[O:10])[CH:7]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.O>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:12]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)(=[O:25])=[O:24])=[C:6]([CH2:8][C:9](=[O:10])[N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 31268PyrrolidineHCID 2724699PyBOPHCID 53234452HCID 53234452、化合物

生成物 1

HCID 673118744-Amino-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)-2-(2-oxo-2-(pyrrolidin-1-yl)ethyl)benzenesulfonamide収率 7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 2-(5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetic acid (360 mg, 1 mmol) and pyrrolidine (0.5 mL, 6 mmol) in 10 mL of DMF was added PyBOP (780 mg, 1.5 mmol) and TEA (0.5 mL, 3.56 mmol). The reaction mixture was stirred for 16 hours. After water was added, the reaction mixture was extracted with ethyl acetate and washed with water, 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated. The crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the desired product as a white powder (28 mg, yield 7%). MS calcd for (C19H22BN3O5S): 415.1. MS found (ESI negative): (M−H)−=414.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.77 (s, 1H), 9.17 (bs, 1H), 7.44 (m, 2H), 7.23 (d, J=8 Hz, 1H), 7.11 (dd, J=8, 2 Hz, 1H), 6.37 (m, 2H)), 4.87 (s, 2H), 3.82 (s, 2H), 3.32 (m, 4H), 1.81 (m, 4H).

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water, 1N HCl and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude residue was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

出典と根拠

ORDレコード
ord-ab8c9e9ac43443ebb2af219fea3f96eb
出典データセット
uspto-grants-2013_06
特許番号
US08461134B2

反応ノート

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