Sulfuric Acid → N-Benzyloxycarbonyl 2-chloro-4,5-dihydroxyphenylglycine

HRID 1788826ノート

反応式

HRID 1788826 の反応式
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:8]=[C:9]([OH:14])[C:10](=[CH:12][CH:13]=1)[OH:11].[CH2:15]([O:22][C:23]([NH:25][CH:26](O)[C:27]([OH:29])=[O:28])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C(O)(=O)C>[CH2:15]([O:22][C:23]([N:25]([C:13]1[CH:12]=[C:10]([OH:11])[C:9]([OH:14])=[CH:8][C:7]=1[Cl:6])[CH2:26][C:27]([OH:29])=[O:28])=[O:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 164964-ChlorocatecholHCID 35095062-(((Benzyloxy)carbonyl)amino)-2-hydroxyacetic acid

生成物 1

HCID 54341029N-Benzyloxycarbonyl 2-chloro-4,5-dihydroxyphenylglycine

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Acetic acid (27 ml), concentrated sulphuric acid (3 ml) then 4-chlorocatechol (5.06 g. 35 mmole) were added to N-benzyloxycarbonyl 2-hydroxyglycine (6.75 g, 30 mmole) cooled in an ice bath. The mixture was stirred for one hour then poured onto ice and ethyl acetate and adjusted to pH7 with saturated sodium carbonate solution. The aqueous layer was collected, washed with ethyl acetate (100 ml), acidified to pH2 and extracted with ethyl acetate (3×75 ml). The extracts were washed with water (2×75 ml) and brine (50 ml) dried and evaporated to a gum which was crystallised from chloroform-cyclohexane, 5.90 g, 56%, mp 144°-145°, δ[(CD3)2CO] 5.06 (2H, s, OCH2), 5.64(1H, d, J8 Hz, CHNH), 6.6-7.0(1H, m, NH), 6.87 and 6.93(2H, 2×s, Ar), 7.30(5H, s, Ph) 8.0-9.4(3H, broad, 2×OH, CO2H). Found: C. 54.29; H, 4.04; Cl, 9.71; N, 4.07%. C16H14ClNO6 requires C, 54.63; H, 4.01; Cl, 10.08; N, 3.98%.

後処理

  1. temperaturecooled in an ice bath
  2. customThe aqueous layer was collected
  3. washwashed with ethyl acetate (100 ml)
  4. extractionextracted with ethyl acetate (3×75 ml)
  5. washThe extracts were washed with water (2×75 ml) and brine (50 ml)
  6. customdried
  7. customevaporated to a gum which
  8. customwas crystallised from chloroform-cyclohexane, 5.90 g, 56%, mp 144°-145°, δ[(CD3)2CO] 5.06 (2H, s, OCH2), 5.64(1H

出典と根拠

ORDレコード
ord-87ff1aaf786d4dafa35d8815afcd33ec
出典データセット
uspto-grants-1987_08
特許番号
US04684639

反応ノート

読み込み中…