Sodium Hydroxide → (2S)-4-[bis(2-{[(tert-butoxy)carbonyl]amino}ethyl)carbamothioyl]-2-{[(tert-butoxy)carbonyl]amino}butanoic acid

HRID 1923974ノート

反応式

HRID 1923974 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:12]([CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]([O:19]C)=[O:18])=[S:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:35]([O:34][C:32]([NH:31][CH2:30][CH2:29][N:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:12]([CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:17]([OH:19])=[O:18])=[S:13])=[O:33])([CH3:36])([CH3:37])[CH3:38]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 59366732methyl (2S)-4-[bis(2-{[(tert-butoxy)carbonyl]amino}ethyl)carbamothioyl]-2-{[(tert-butoxy) carbonyl]amino}butanoate

生成物 1

HCID 59366983(2S)-4-[bis(2-{[(tert-butoxy)carbonyl]amino}ethyl)carbamothioyl]-2-{[(tert-butoxy)carbonyl]amino}butanoic acid収率 88.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To the solution of the ester XV (290 mg, 0.51 mmol) in MeOH (10 mL) was added 4 M NaOH dropwise until pH=13. The mixture was stirred overnight at r.t. before evaporating the MeOH under reduced pressure. The residue was mixed with water and washed with ether. After acidifying to pH˜3 with 2 M HCl, the product was extracted with DCM, dried over MgSO4 and concentrated under vacuum to give (2S)-4-[bis(2-{[(tert-butoxy)carbonyl]amino}ethyl)carbamothioyl]-2-{[(tert-butoxy)carbonyl]amino}butanoic acid XVI (250 mg, 0.45 mmol, 88% yield). ESIMS found for C24H44N4O8S m/z 549 (M+H).

後処理

  1. custombefore evaporating the MeOH under reduced pressure
  2. additionThe residue was mixed with water
  3. washwashed with ether
  4. extractionthe product was extracted with DCM
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-098228d0c9694843b46de188715445b8
出典データセット
uspto-grants-2012_05
特許番号
US08178490B2

反応ノート

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