Acetone → HCID 68973767, compound

HRID 1272693Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:43])[C@@H:4]([NH:13][C:14]([C:16]1[N:17]=[C:18]([CH2:37][CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)[C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[C:21]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=1)[CH:20]=2)=[O:15])[CH2:5][C:6]1[S:7]C(C=C)=[CH:9][CH:10]=1.O.C[N+]1([O-])CC[O:49]CC1.C(OCC)(=O)C.[CH3:59][C:60]([CH3:62])=[O:61]>[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3](=[O:43])[C@@H:4]([NH:13][C:14]([C:16]1[N:17]=[C:18]([CH2:37][CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)[C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[C:21]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=1)[CH:20]=2)=[O:15])[CH2:5][C:6]1[S:7][C:59]([CH:60]([OH:61])[CH2:62][OH:49])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2(S)-{[7-(4-tert-Butyl-phenoxy)-1-cyclopentylmethyl-isoquinoline-3-carbonyl]-amino}-3-(5-vinylthiophen-2-yl)-propionic acid methyl ester (prepared in Example 9) (0.650 g, 1.09 mmol) in acetone:water was added methylmorpholine-N-oxide (0.340 mL) and osmium tetroxide (2 crystals). The solution was stirred at 0° C. for 1.5 h. Ethyl acetate was added and extracted with a solution of Na2S2O4(satd), brine, dried (Na2SO4), and concentrated under reduced pressure to give 0.600 g of 2(S)-{[7-(4-tert-Butyl-phenoxy)-1-cyclopentylmethyl-isoquinoline-3-carbonyl]-amino}-3-[5-(1,2-dihydroxy-ethyl)-thiophen-2-yl]-propionic acid methyl ester.

Workup

extractionextracted with a solution of Na2S2O4(satd), brine
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e8815da5aac44aa0ba1f5fbaf9fa0ee8
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208601B2

Reaction notes

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