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Tetrahydrofuran → N-Boc-N'-trityl-L-histidine

HRID 852858
ノート
印刷プレビュー

反応式

HRID 852858 の反応式
C([O:8][C:9](=[O:44])[CH:10]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:11][C:12]1[N:13]=[CH:14][N:15]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=1)C1C=CC=CC=1.[OH-].[K+].C1COCC1>CO.O>[C:40]([O:39][C:37]([NH:36][CH:10]([CH2:11][C:12]1[N:13]=[CH:14][N:15]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=1)[C:9]([OH:44])=[O:8])=[O:38])([CH3:43])([CH3:41])[CH3:42]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 694170642-tert-Butoxycarbonylamino-3-(1-trityl-1H-imidazol-4-yl)-propionic acid benzyl ester

生成物 1

HCID 3437537N-Boc-N'-trityl-L-histidine収率 94.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 962
Water
溶媒

実験手順

2-tert-Butoxycarbonylamino-3-(1-trityl-1H-imidazol-4-yl)-propionic acid benzyl ester (6 g, 10.22 mmol) in MeOH (20 mL) was added potassium hydroxide (1.14 g, 20.44 mmol) in water (10 mL). THF (25 mL) was added to homogenise the solution. The solution was stirred for 1 hour and the solvents removed. Water was added and extracted with Et2O. The aqueous layer was acidified with dilute aqueous HCl and extracted with Et2O. The Et2O was washed with water, brine, dried over MgSO4 and filtered. The solvent was removed to give the title compound (4.792 g, 94%). ESMS 498 (M+H+) Mpt 101.5-103.6° C. 1H NMR (CDCl3) δ 1.35 (9H, s), 3.25 (1H, dd, J=5.37, 14.9), 3.39 (1H, dd, J=4.83, 14.9), 4.46-4.52 (1H, m), 5.66, (1H, d, J=5.91), 6.83 (1H, s), 7.07-7.10 (3H, m), 7.26-7.30 (8H, m), 7.42-7.45 (4H, m), 8.13 (1H, s). 13C NMR (CDCl3) δ 28.26, 29.00, 53.07, 76.14, 78.98, 120.88, 128.21, 128.32, 129.63, 133.68, 137.22, 141.52, 154.90, 173.60.

後処理

  1. stirringThe solution was stirred for 1 hour
  2. customthe solvents removed
  3. additionWater was added
  4. extractionextracted with Et2O
  5. extractionextracted with Et2O
  6. washThe Et2O was washed with water, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customThe solvent was removed

出典と根拠

ORDレコード
ord-373f0b850ba14dbe8c919b8b0681cd62
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07253194B2

反応ノート

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