Acetic Acid → diphenylmethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate

HRID 2230399ノート

反応式

HRID 2230399 の反応式
Cl.[OH:2][C@@H:3]([C@H:18]([OH:33])[C@H:19]([OH:32])[C@@H:20]([NH:23][C:24](=[O:31])[C@H:25]([CH2:27][CH:28]([CH3:30])[CH3:29])[NH2:26])[CH2:21][OH:22])[C:4]([NH:6][C@H:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][C:9]([OH:11])=[O:10])=[O:5].[C:34]1([C:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[N+]=[N-])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(O)(=O)C>CO>[OH:2][C@@H:3]([C@H:18]([OH:33])[C@H:19]([OH:32])[C@@H:20]([NH:23][C:24](=[O:31])[C@H:25]([CH2:27][CH:28]([CH3:29])[CH3:30])[NH2:26])[CH2:21][OH:22])[C:4]([NH:6][C@H:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][C:9]([O:11][CH:40]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:10])=[O:5]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 69823761(S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid hydrochloride

生成物 1

HCID 11039599diphenylmethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate収率 88.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a solution of (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid hydrochloride (1.84 g) in methanol (40 ml) was added a solution of diphenyldiazomethane (1.45 g) in methanol (20 ml) and the mixture was stirred at room temperature for 4 hours. After addition of acetic acid (0.1 ml), the reaction mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogencarbonate solution and saturated brine respectively and the ethyl acetate solution was dried over anhydrous sodium sulfate. Removal of the organic solvent gave a residue, which was purified by silica gel column chromatography. Elution with ethyl acetate-methnaol (2:1) provided the title compound (2.05 g).

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with aqueous sodium hydrogencarbonate solution and saturated brine respectively
  3. dry with materialthe ethyl acetate solution was dried over anhydrous sodium sulfate
  4. customRemoval of the organic solvent
  5. customgave a residue, which
  6. customwas purified by silica gel column chromatography
  7. washElution with ethyl acetate-methnaol (2:1)

出典と根拠

ORDレコード
ord-4885b49164ca4211882b5fbd7af72d48
出典データセット
uspto-grants-2002_07
特許番号
US06423869B1

反応ノート

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