Iodine → HCID 59909851, compound

HRID 2183031Notes

Reaction equation

HRID 2183031 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C.[CH:29]1([CH2:35][CH2:36][CH2:37][C@@H:38]([C:47]([NH:49][CH:50]([C:54]([O:56][CH3:57])=[O:55])[C:51](=[O:53])[CH3:52])=O)[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>O1CCCC1.O>[C:43]([O:42][C:40](=[O:41])[CH2:39][C@H:38]([C:47]1[O:53][C:51]([CH3:52])=[C:50]([C:54]([O:56][CH3:57])=[O:55])[N:49]=1)[CH2:37][CH2:36][CH2:35][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)([CH3:44])([CH3:46])[CH3:45]

Participants

7

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 59909746HCID 59909746, compound

Product 1

HCID 59909851HCID 59909851, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A suspension of triphenylphosphine (9.49 g, 36.18 mmol), iodine (7.98 g, 31.44 mmol) and triethylamine (8.49 ml, 60.75 mmol) in tetrahydrofuran was cooled to −78° C. then treated with tert-butyl (3R)-6-cyclohexyl-3-({[1-(methoxycarbonyl)-2-oxopropyl]amino}carbonyl)hexanoate (Preparation 68) (4.86 g, 11.80 mmol) over 15 minutes. The mixture was stirred at −78° C. for 30 minutes then at 0-5° C. for 2 hours. The mixture was diluted with water and extracted with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:pentane (0:100 to 10:90) to afford the title compound as a colourless oil (2.92 g).

Workup

  1. waitat 0-5° C. for 2 hours
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate:pentane (0:100 to 10:90)

Sources & evidence

ORD record
ord-e3977aefc3104ac48d5042bc1b54308e
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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