Trimethylphosphine → HCID 86612070, compound

HRID 2253413Notes

Reaction equation

HRID 2253413 reaction equation
[NH2:1][C@H:2](/[C:29](/[CH3:37])=[CH:30]/[C:31]1[N:32]=[C:33]([CH3:36])[S:34][CH:35]=1)[CH2:3][C@@H:4]1[O:28][C@:5]1([CH3:27])[CH2:6][CH2:7][C:8](=[O:26])[C@H:9]([CH3:25])[C@H:10]([OH:24])[C@@H:11]([CH3:23])[C:12](=[O:22])[C:13]([CH3:21])([CH3:20])[C@@H:14]([OH:19])[CH2:15][C:16]([OH:18])=[O:17].N([C@H](/C(/C)=C/C1N=C(C)SC=1)C[C@@H]1O[C@]1(C)CCC(=O)[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(O)=O)=[N+]=[N-].CP(C)C>C1COCC1.O.C1(C)C=CC=CC=1>[NH2:1][C@H:2](/[C:29](/[CH3:37])=[CH:30]/[C:31]1[N:32]=[C:33]([CH3:36])[S:34][CH:35]=1)[CH2:3][C@@H:4]1[O:28][CH:15]([C:16]([OH:18])=[O:17])[C@@H:14]([OH:19])[C:13]([CH3:21])([CH3:20])[C:12](=[O:22])[C@H:11]([CH3:23])[C@@H:10]([OH:24])[C@@H:9]([CH3:25])[C:8](=[O:26])[CH2:7][CH2:6][C@H:5]1[CH3:27]

Participants

6

Reactant 3

HCID 68983TrimethylphosphineHCID 59645497HCID 59645497, compoundHCID 86584891HCID 86584891, compound

Product 1

HCID 86612070HCID 86612070, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

(35,6R,7S,8R,12R, 13S,15S,16E)-15-amino-3,7-dihydroxy-5,9-dioxo-12,13-epoxy-4,4,6,8,12,16-hexamethyl-17-(2-methylthiazol-4-yl)-16-heptadecenoic acid. A solution of (3S,6R,7S,8R,12R,13S,15S,16E)-15-azido-3,7-dihydroxy-5,9-dioxo-12,13-epoxy-4,4,6,8,12,16-hexamethyl-17-(2-methylthiazol-4-yl)-16-heptadecenoic acid (565 mg) in 15 mL of THF/water (10:1 v/v) is treated with a 1.0 M solution of trimethylphosphine in toluene (3 mL) under argon for 2 hours at ambient temperature. The mixture is concentrated, and the product is purified by flash chromatography on SiO2.

Workup

  1. concentrationThe mixture is concentrated
  2. customthe product is purified by flash chromatography on SiO2

Sources & evidence

ORD record
ord-fec5a2c100fa4f04bb02b5b6c61d1749
Source dataset
uspto-grants-2008_01
Patent number
US07323573B2

Reaction notes

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