Sodium Iodide → HCID 131734844, compound

HRID 1779158Notes

Reaction equation

HRID 1779158 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:22][C:23]([C@H:25]([C@@:43]([OH:55])([CH2:51][C:52]([O-:54])=[O:53])[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])/[CH:26]=[CH:27]/[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34](=[O:42])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:24])[C:14]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[C:56]([O:59][CH2:60][CH2:61]Br)(=[O:58])[CH3:57].C(N(CC)C(C)C)(C)C.[I-].[Na+].[Cl-].[NH4+]>ClCCl>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:22][C:23]([C@H:25]([C@@:43]([OH:55])([CH2:51][C:52]([O:54][CH:60]([O:59][C:56](=[O:58])[CH3:57])[CH3:61])=[O:53])[C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])/[CH:26]=[CH:27]/[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34](=[O:42])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:24])[C:14]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[O:15])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 135641-Acetoxy-2-bromoethaneHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 131734845HCID 131734845, compound

Product 1

HCID 131734844HCID 131734844, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

1-tert-Butyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonylmethoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate (18 mg, 0.0233 mmol) was dissolved in dichloromethane (1.8 mL), and bromoethyl acetate (8.2 μL, 0.0700 mmol), N,N-diisopropylethylamine (12.2 μL, 0.0700 mmol), and sodium iodide (10.5 mg, 0.0700 mol) were added. The mixture was stirred at 40° C. for 19 hours and cooled to room temperature, and a saturated aqueous solution of ammonium chloride (15 mL) was then added. After ethyl acetate extraction, the organic layer was dried over anhydrous sodium sulfate. The solvent was then distilled off to obtain 19 mg of crude 1-tert-butyl 4-(1-acetoxy-ethyl) (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonylmethoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate. The obtained crude product was used in the next reaction without further purification (ESI (LC/MS positive mode) m/z 858 (M+H); Rt 2.82 min.).

Workup

  1. temperaturecooled to room temperature
  2. extractionAfter ethyl acetate extraction
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-1311bc9abf7943c7824c67ec81240fdb
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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