ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Methanol → tert-butyl (2S,4S)-4-(benzyloxymethyl)-1-hydroxy-5-methylhexan-2-ylcarbamate

HRID 507836
ノート
印刷プレビュー

反応式

HRID 507836 の反応式
[CH2:1]([O:8][CH2:9][C@H:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][C@H:12]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13]C(OC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].C[OH:32]>O1CCCC1>[CH2:1]([O:8][CH2:9][C@H:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][C@H:12]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:13][OH:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 68623312methyl 4(S)-benzyloxymethyl-2(S)-tert-butoxycarbonylamino-5-methylhexanecarboxylate

生成物 1

HCID 70642503tert-butyl (2S,4S)-4-(benzyloxymethyl)-1-hydroxy-5-methylhexan-2-ylcarbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The stirred solution of 5.0 g of methyl 4(S)-benzyloxymethyl-2(S)-tert-butoxycarbonylamino-5-methylhexanecarboxylate [CAS 180182-92-7] in 80 ml of tetrahydrofuran is admixed in portions with 0.660 g of lithium borohydride. The reaction mixture is stirred for another 3 hours, admixed cautiously with 25 ml of methanol and concentrated by evaporation at 40° C. The residue is dissolved once more in 70 ml of methanol and again concentrated by evaporation at 40° C. The residue is admixed with 1M HCl (cold) and extracted with dichloromethane (3×). The combined organic phases are washed with water, dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a colourless oil. Rf=0.32 (1:1 EtOAc-heptane); Rt=4.86 (gradient I).

後処理

  1. concentrationconcentrated by evaporation at 40° C
  2. dissolutionThe residue is dissolved once more in 70 ml of methanol
  3. concentrationagain concentrated by evaporation at 40° C
  4. extractionextracted with dichloromethane (3×)
  5. washThe combined organic phases are washed with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-e034e51d4304480183ff755b96f9a76d
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07786307B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート