Trifluoroacetic acid → N-[(1S,2S)-2-[(3R,5S,6R)-6-(2,2-dimethyl-propoxy)-5-methyl-morpholin-3-yl]-2-hydroxy-1-(3-hydroxy-benzyl)-ethyl]-acetamide trifluoroacetate

HRID 20467ノート

反応式

HRID 20467 の反応式
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([N:15]1[C@@H:20]([C@@H:21]([OH:35])[C@@H:22]([NH:31][C:32](=[O:34])[CH3:33])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)[CH2:19][O:18][C@@H:17]([O:36][CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C@@H:16]1[CH3:42])=O)(C)(C)C>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:40][C:38]([CH3:39])([CH3:41])[CH2:37][O:36][C@H:17]1[C@H:16]([CH3:42])[NH:15][C@@H:20]([C@@H:21]([OH:35])[C@@H:22]([NH:31][C:32](=[O:34])[CH3:33])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)[CH2:19][O:18]1

参加物

3

反応物 2

HCID 6422Trifluoroacetic acidHCID 68563074HCID 68563074、化合物

生成物 1

HCID 68563032N-[(1S,2S)-2-[(3R,5S,6R)-6-(2,2-dimethyl-propoxy)-5-methyl-morpholin-3-yl]-2-hydroxy-1-(3-hydroxy-benzyl)-ethyl]-acetamide trifluoroacetate

実験手順

Add trifluoroacetic acid (3 mL) to (2R,3S,5R)-5-[(1S,2S)-2-acetylamino-1-hydroxy-3-(3-hydroxy-phenyl)-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester (84 mg, 0.17 mmol). Stir 40 minutes and evaporate to give N-[(1S,2S)-2-[(3R,5S,6R)-6-(2,2-dimethyl-propoxy)-5-methyl-morpholin-3-yl]-2-hydroxy-1-(3-hydroxy-benzyl)-ethyl]-acetamide trifluoroacetate (115 mg). Add diisopropylethyl-amine (0.074 mL, 0.425 mmol) dropwise to an ice cold solution of N-[(1S,2S)-2-[(3R,5S,6R)-6-(2,2-dimethyl-propoxy)-5-methyl-morpholin-3-yl]-2-hydroxy-1-(3-hydroxy-benzyl)-ethyl]-acetamide (115 mg) and benzyl chloroformate (0.029 mL, 0.20 mmol) in tetrahydrofuran (4 mL). Stir 30 minutes and add an additional portion of diisopropylethylamine (0.074 mL) and benzyl chloroformate (0.025 mL). Stir 50 minutes and warm to ambient temperature, stir 10 minutes and dilute with saturated aqueous sodium chloride followed by ethyl acetate and 1N aqueous hydrochloric acid. Separate layers and wash organic phase with saturated aqueous sodium chloride, dry with magnesium sulfate. Purify on silica gel with dichloromethane/ethyl acetate mixtures to give the desired compound (69 mg) as a white foam. MS(ESI): m/z=529 [M+H]+.

後処理

  1. customevaporate

出典と根拠

ORDレコード
ord-1d9a20d92ea24d6d909236847603dd0f
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

反応ノート

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