Tetrahydrofuran → HCID 131724974, compound

HRID 1070437Notes

Reaction equation

HRID 1070437 reaction equation
Cl.C([N:9]1[CH2:36][CH2:35][CH2:34][C@@:10]1([CH3:37])[C:11]([NH:13][C@H:14]([C:31]([OH:33])=[O:32])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]#[N:30])=[CH:18][CH:17]=1)=[O:12])(OC(C)(C)C)=O.[Cl:38][C:39]1[CH:40]=[C:41]([S:46](Cl)(=[O:48])=[O:47])[CH:42]=[C:43]([Cl:45])[CH:44]=1.O1CCC[CH2:51]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:38][C:39]1[CH:40]=[C:41]([S:46]([N:9]2[CH2:36][CH2:35][CH2:34][C@@:10]2([CH3:37])[C:11]([NH:13][C@H:14]([C:31]([O:33][CH3:51])=[O:32])[CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]#[N:30])=[CH:20][CH:21]=2)=[O:12])(=[O:48])=[O:47])[CH:42]=[C:43]([Cl:45])[CH:44]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 131724975HCID 131724975, compound

Product 1

HCID 131724974HCID 131724974, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 95 mg of N-Boc-2-(S)-methyl-(L)-prolyl-4-(2-cyanophenoxy)-phenylalanine, hydrochloride, 61 mg 3,5-dichlorobenzenesulfonyl chloride, and 2.5 mL of tetrahydrofuran at 0° C. was added 110 uL of diisopropylethylamine via syringe. The reaction was allowed to warm to room temperature and run at said temperature overnight. The reaction was diluted with methylene chloride, washed with water, 1N hydrochloric acid, saturated sodium bicarbonate solution, and saturated salt solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The product was purified via silica gel chromatography, eluted with 80% hexane:20% acetone to yield 62 mg of of N-(3,5-dichlorobenzenesulfonyl)-2-(S)-methyl-(L)-prolyl-4-(2-cyanophenoxy)-phenylalanine, methyl ester.

Workup

  1. customtemperature overnight
  2. washwashed with water, 1N hydrochloric acid, saturated sodium bicarbonate solution, and saturated salt solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe product was purified via silica gel chromatography
  6. washeluted with 80% hexane

Sources & evidence

ORD record
ord-e341faa4b67b4ff8975acae0979bffb3
Source dataset
uspto-grants-2005_06
Patent number
US06903075B1

Reaction notes

Loading…