Sodium Iodide → HCID 88259081, compound

HRID 1952736Notes

Reaction equation

HRID 1952736 reaction equation
S(O[CH2:6][C@@H:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=O)(=O)C.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[SH:33].[CH:34](N(C(C)C)CC)(C)C.[I-].[Na+]>C(Cl)Cl.CN(C)C=O>[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[S:33][C:6]1[CH:7]=[CH:16][C:17]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:34]=1.[C:9]([NH:8][C@@H:7]([CH2:6][SH:33])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 70582-NaphthalenethiolHCID 81531DiisopropylethylamineHCID 13857264HCID 13857264, compound

Product 1

HCID 88259081HCID 88259081, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-Boc-D-phenylalaninol mesylate (0.3 g, 0.9 mmol), dimethylformamide (10 mL), 2-napthalenethiol (0.22 g, 1.39 mmol), diisopropylethylamine (1.39 mmol) and sodium iodide (0.14 g, 0.93 mmol) was kept at 80 ° C. for 18 hr, cooled to room temperature and methylene chloride (25 ml) was added. This mixture was washed with water (2×10 mL), 1M sodium hydroxide (3×10 mL) and brine (2×15 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate adsorbed onto silica gel and applied to a column prepacked with silica gel. The title compound (121 mg) was eluted with hexane:ethyl acetate (90:10, v:v) to afford a white solid.

Workup

  1. washThis mixture was washed with water (2×10 mL), 1M sodium hydroxide (3×10 mL) and brine (2×15 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. washThe title compound (121 mg) was eluted with hexane:ethyl acetate (90:10, v:v)
  5. customto afford a white solid

Sources & evidence

ORD record
ord-1ffc3ff76205462f8f338a003c2478dc
Source dataset
uspto-grants-2000_09
Patent number
US06114310

Reaction notes

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