Tetrahydrofuran → HCID 69415552, compound

HRID 852846Notes

Reaction equation

HRID 852846 reaction equation
C([O:8][C:9](=[O:36])[CH:10]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:13]=1)C1C=CC=CC=1.[OH-].[K+].C1COCC1>CO.O>[CH2:21]([N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([CH2:11][C@@H:10]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:9]([OH:36])=[O:8])=[CH:13]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 69414735HCID 69414735, compound

Product 1

HCID 69415552HCID 69415552, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 3-(1-benzyl-1H-indol-3-yl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester (2.1 g. 4.3 mmol) in MeOH (10 mL) was added KOH (0.740 g, 12.9 mmol) in water (5 mL). THF (5 mL) was added until the solution became homogenous. The solution was stirred until completion (about 2 h). 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 (1.555 g, 91%). ESMS 395 (M+H+), mp 163.8-165.4° C. (EtOAc/petroleum ether). 1H NMR (DMSO-d6) δ 7.56 (1H, d, J=7.83 Hz), 7.39-6.99 (10H, m), 6.65 (1H, d), 4.18 (1H, m), 5.36 (2H, s), 3.15 (1H, dd, J=4.67, 14.56 Hz), 2.99 (1H, dd, J=9.18, 14.56 Hz), 1.32 (9H, s). 13C NMR (DMSO-d6) δ 174.0, 155.2, 137.6, 136.4, 128.7, 127.5, 127.2, 126.7, 126.6, 121.7, 119.3, 119.2, 109.7, 109.6, 79.4, 54.1, 49.9, 28.3, 27.7. ISMS: 395 (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-fd8958a1cd874ee2be0dbf446a4f691f
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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