Tetrahydrofuran → HCID 69417029, compound

HRID 852847Notes

Reaction equation

HRID 852847 reaction equation
C([O:8][C:9](=[O:38])[CH:10]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH:22]=[CH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:13]=1)C1C=CC=CC=1.[OH-].[K+].C1COCC1>CO.O>[C:34]([O:33][C:31]([NH:30][C@H:10]([CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][CH:22]=[CH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:13]=1)[C:9]([OH:38])=[O:8])=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 69414706HCID 69414706, compound

Product 1

HCID 69417029HCID 69417029, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 2-tert-butoxycarbonylamino-3-[1-(3-phenyl-allyl)-1H-indol-3-yl]-propionic acid benzyl ester (6.483 g. 12.71 mmol) in MeOH (25 mL) was added KOH (2.4 g, 42.86 mmol) in water (10 mL). THF (30 mL) was added until the solution became homogenous. The solution was stirred until completion (overnight). Volatile solvents were removed and the residue taken up into CH2Cl2 and water. The aqueous layer was carefully acidified with dilute aqueous HCl and extracted with-Et2O. The Et2O was washed with water and brine and then dried with MgSO4. The solution was filtered and the solvent removed to afford the required material without further purification (5.27 g, quantitative). ESMS 421 (M+H+) 1H NMR (DMSO-d6) δ 7.56-6.88 (11H, m), 6.47 (1H, d, 15.85 Hz), 6.40 (1H, dt, J=5.4, 15.85 Hz), 4.91 (2H, d, J=5Hz), 4.14 (1H, m), 3.15 (1H, m), 2.99 (1H, m), 1.29 (9H, s). 13C NMR (DMSO-d6) δ 173.8, 155.3, 136.1, 135.9, 131.4, 128.6, 127.9, 127.7, 126.8, 126.3, 125.8, 121.1, 118.6, 110.3, 109.9, 77.9, 54.6, 47.4, 28.1, 26. 8. ISMS: 421 (M+H),

Workup

  1. customVolatile solvents were removed
  2. extractionextracted with-Et2O
  3. washThe Et2O was washed with water and brine
  4. dry with materialdried with MgSO4
  5. filtrationThe solution was filtered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-17e13ddcfee645d498463ba32e7bb2f9
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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