Triphenylphosphine → HCID 59619419, compound

HRID 1367557Notes

Reaction equation

HRID 1367557 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[Cl:24])(=[O:16])=[O:15])[CH2:11][C@H:10]2[CH2:25][OH:26])=[O:8])[CH2:5][CH2:4]1)#[N:2].[Cl:27][C:28]1[CH:33]=[CH:32][C:31](O)=[CH:30][N:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C>ClCCl.O1CCCC1>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[Cl:24])(=[O:15])=[O:16])[CH2:11][C@H:10]2[CH2:25][O:26][C:31]2[CH:30]=[N:29][C:28]([Cl:27])=[CH:33][CH:32]=2)=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 8198212-Chloro-5-hydroxypyridineHCID 59619202HCID 59619202, compound

Product 1

HCID 59619419HCID 59619419, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cold mixture (ice bath) of (1R,2R,4S)-4-(2-chloro-4-fluoro-benzenesulfonyl)-2-hydroxymethyl-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (example 155, 28.5 mg), 2-chloro-5-hydroxypyridine (19 mg) and triphenyl phosphine (28 mg) in dichloromethane (1 mL) was added a solution of di-tert-butyl-azodicarboxylate (25 mg) in tetrahydrofuran (1 mL). The reaction mixture was stirred overnight then adsorbed unto silica and was purified by flash chromatography on silica gel with a gradient of cyclohexane:ethyl acetate (4:1 to 1:1 v/v) as eluant to afford the title compound (14 mg, 36%) as a colorless solid. MS (EI): 512.0 (M+H)+.

Workup

  1. customwas purified by flash chromatography on silica gel with a gradient of cyclohexane:ethyl acetate (4:1 to 1:1 v/v) as eluant

Sources & evidence

ORD record
ord-c91812637d0a417ab75becb3567082e5
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

Loading…