Sodium Iodide → HCID 131714420, compound

HRID 652349Notes

Reaction equation

HRID 652349 reaction equation
Cl.[NH2:2][C@H:3]([C:8]([NH:10][C@H:11]([C:15]([NH:17][C@H:18]([C:26]([O:28][CH3:29])=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH:12]([CH3:14])[CH3:13])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6].[I-].[Na+].S(=O)(O)[O-].[Na+].[C:37](=O)(O)[O-].[Na+].ClCC(CCl)=O.[C:48]1([CH2:54][O:55][C:56]([NH:58][C@H:59]([C:64]([OH:66])=O)[CH2:60][CH:61]([CH3:63])[CH3:62])=[O:57])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C)C=O.C(OCC)(=O)C>[C:48]1([CH2:54][O:55][C:56]([NH:58][C@@H:59]([CH2:60][CH:61]([CH3:62])[CH3:63])[C:64](=[O:66])[CH2:37][NH:2][C@H:3]([C:8]([NH:10][C@H:11]([C:15]([NH:17][C@H:18]([C:26]([O:28][CH3:29])=[O:27])[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:16])[CH:12]([CH3:14])[CH3:13])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6])=[O:57])[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 88326106HCID 88326106, compoundHCID 131714421HCID 131714421, compound

Product 1

HCID 131714420HCID 131714420, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 428 mg (1 mmol) of L-leucyl-L-valyl-L-phenylalanine, methyl ester, hydrochloride, 150 mg (1 mmol) of sodium iodide and 19 mg (0.1 mmol) of sodium bisulfite (on the basis of this experiment, its use was abandoned in the preparation of other compounds) was treated with 1 ml of dry dimethylformamide under argon at room temperature. Solid sodium bicarbonate (176 mg, 2.1 mmol) was added followed by a solution of 298 mg (1 mmol) of [(phenylmethoxy)carbonyl]-L-leucine chloromethyl ketone in 1 ml of dimethylformamide. After stirring for 24 hours at room temperature, the reaction was diluted with 50 ml of ethyl acetate and rinsed with two 10 ml portions of water, 10 ml of dilute aqueous sodium bisulfite, two 10 ml portions of water and brine, dried (magnesium sulfate) and concentrated in vacuo to 580 mg of crude product. Flash chromatography on 40 g of LPS-1 silica gel using 5:1, petroleum ether:acetone yielded 263 mg of the title compound as an oil.

Workup

  1. customwas abandoned in the preparation of other compounds)
  2. washrinsed with two 10 ml portions of water, 10 ml of dilute aqueous sodium bisulfite, two 10 ml portions of water and brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated in vacuo to 580 mg of crude product

Sources & evidence

ORD record
ord-a536a97ee65b47d2b76a24ff9db68b33
Source dataset
uspto-grants-1987_06
Patent number
US04670541

Reaction notes

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