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

HRID 852858
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HRID 852858 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

HCID 3437537N-Boc-N'-trityl-L-histidine수율 94.2%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 962
Water
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-373f0b850ba14dbe8c919b8b0681cd62
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07253194B2

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