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

HRID 571163노트

반응식

HRID 571163 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 1983AcetaminophenHCID 23666486Sodium TaurateHCID 594879154-Acetamidophenyl 4-nitrophenyl carbonate2회

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

((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]−.

후처리

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

출처 및 근거

ORD 기록
ord-0501c7320e3e4abc961c43f0827207aa
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024055B2

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