1,4-Dioxane → HCID 10482868, compound

HRID 1781198Notes

Reaction equation

HRID 1781198 reaction equation
C[CH:2]([C:39]([O-:41])=[O:40])[N:3]([C:12](=[O:38])[CH:13]([CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1)[NH:14][C:15]([O:17][CH:18]1[CH:25]2[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:27][CH:19]1[CH2:20]3)[CH2:24]2)=[O:16])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O1CCOC[CH2:43]1>O>[NH:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29]([CH2:28][C:13]([CH3:43])([NH:14][C:15]([O:17][CH:18]2[CH:19]3[CH2:20][CH:21]4[CH2:22][CH:23]([CH2:24][CH:25]2[CH2:26]4)[CH2:27]3)=[O:16])[C:12]([N:3]([CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][C:39]([OH:41])=[O:40])=[O:38])=[CH:30]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 86750865HCID 86750865, compound

Product 1

HCID 10482868HCID 10482868, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of methyl N-[α-methyl-N-[(tricyclo[3.3.1.13,7 ]dec-2-yloxycarbonyl)-DL-tryptophyl]-N-(2-phenylethyl)glycinate (285 mg, 0.5 mmol) in dioxane (10 mL) and water (5 mL) was added lithium hydroxide-1-hydrate (42 mg, 1.0 mmol) and the resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated, acidified with dilute HCl, and extracted with ethyl acetate (2×50 mL). After drying over magnesium sulfate and concentration, flash column chromatography yielded the title compound which was crystallized from ethyl acetate and hexane to give 80 mg (29%) of white solid, mp 100°-105° C. IR (KBr) 3388 2908, 2855 1710 cm-1 ; NMR (250 MHz DMSO, 70° C.) 1.30 (3H, s), 1.1-1.58 (2H, m), 1.58-2.18 (12H, m), 2.56-2.92 (2H, m), 2.92-3.6 (4H, m), 3.6-4.26 (4H, m), 4.76 (1H, br s), 6.82-7.38 (9H, m), 7.45 (1H, d, J 7.7 Hz), 10.70 (1H, br s).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialAfter drying over magnesium sulfate and concentration, flash column chromatography

Sources & evidence

ORD record
ord-ab45568062e14e43bc0af4cc036d0a63
Source dataset
uspto-grants-1997_05
Patent number
US05631281

Reaction notes

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