Water → 2-((4-Acetamidophenoxy)carbonylamino)ethanesulfonic acid

HRID 571163ノート

反応式

HRID 571163 の反応式
[C:1](=[O:23])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.[NH2:24][CH2:25][CH2:26][S:27]([O-:30])(=[O:29])=[O:28].[Na+].OC1C=CC(NC(=O)C)=CC=1.O>C(#N)C>[C:10]([NH:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][C:1]([NH:24][CH2:25][CH2:26][S:27]([OH:30])(=[O:29])=[O:28])=[O:23])=[CH:8][CH:7]=1)(=[O:12])[CH3:11]

参加物

6

反応物 4

HCID 962WaterHCID 1983AcetaminophenHCID 23666486Sodium TaurateHCID 594879154-Acetamidophenyl 4-nitrophenyl carbonate2 回

生成物 1

HCID 469130472-((4-Acetamidophenoxy)carbonylamino)ethanesulfonic acid

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

((4-Acetamidophenoxy)carbonylamino)ethanesulfonic acid (12a) was prepared according to the General Method for the Reaction of Alkali Metal Salts of Amino Acid Derivatives with 4-Acetamidophenyl 4-Nitrophenyl carbonate (3). A solution of 511 mg (3.48 mmol) of sodium 2-aminoethanesulfonate (7) in approximately one (1) mL of degassed water was reacted with a solution of 4-acetamidophenyl 4-nitrophenyl carbonate (3) (1.10 g, 3.48 mmol) dissolved in 5 mL of acetonitrile (MeCN). After work-up procedures, the aqueous layer was lyophilized off to afford 1.0 g (˜quantitative yield) of the crude 2-((4-acetamidophenoxy)carbonylamino)ethanesulfonic acid (12a) which was used directly and without further isolation or purification procedures. The material thus obtained was contaminated with some sodium chloride (NaCl) and other sodium salts. 1H NMR (300 MHz, D2O): δ 7.22 (d, J=9.0 Hz, 2H), 6.94 (d, J=8.7 Hz, 2H), 3.40 (t, J=6.6 Hz, 2H), 2.95 (t, J=6.6 Hz, 2H), 1.96 (s, 3H). LC/MS (ESI): m/z=303.0 [M+H]+, 602.8 [2M−H]−.

後処理

  1. custom((4-Acetamidophenoxy)carbonylamino)ethanesulfonic acid (12a) was prepared

出典と根拠

ORDレコード
ord-0501c7320e3e4abc961c43f0827207aa
出典データセット
uspto-grants-2015_05
特許番号
US09024055B2

反応ノート

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