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

HRID 852858
Notes
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Reaction equation

HRID 852858 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 962
Water
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-373f0b850ba14dbe8c919b8b0681cd62
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253194B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes