Triphenylphosphine → HCID 53934016, compound

HRID 1377870Notes

Reaction equation

[CH3:1][Si:2]([CH3:41])([C:35]([CH3:40])([CH3:39])[CH:36]([CH3:38])[CH3:37])[O:3][C:4]1[C:21]2[CH2:20][S:19][CH2:18][C@@H:17]([C:22]3[O:26][N:25]=[C:24]([CH3:27])[N:23]=3)[NH:16][C:15](=[O:28])[CH2:14][CH2:13][C@H:12]([CH2:29]O)[CH2:11][O:10][C:9](=[O:31])[C:8]=2[C:7]([CH3:32])=[C:6]([O:33][CH3:34])[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P([N:87]=[N+:88]=[N-:89])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[N:87]([CH2:29][C@@H:12]1[CH2:11][O:10][C:9](=[O:31])[C:8]2[C:7]([CH3:32])=[C:6]([O:33][CH3:34])[CH:5]=[C:4]([O:3][Si:2]([CH3:1])([CH3:41])[C:35]([CH3:40])([CH3:39])[CH:36]([CH3:37])[CH3:38])[C:21]=2[CH2:20][S:19][CH2:18][C@@H:17]([C:22]2[O:26][N:25]=[C:24]([CH3:27])[N:23]=2)[NH:16][C:15](=[O:28])[CH2:14][CH2:13]1)=[N+:88]=[N-:89]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 140 mg of (4R,9R)-16-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-9-hydroxymethyl-14-methoxy-13-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecin-6,12-dione and 121 mg of triphenyl-phosphine in 2 ml of tetrahydrofuran were added at 0° C. 80 mg of diethyl azodicarboxylate and 127 mg of diphenylphosphoryl azide. The mixture was stirred at 0° C. for 35 min and then evaporated in vacuo. The residue was chromatographed on silica gel using ethyl acetate/hexane (1:1, v/v) as eluent, to yield (4R,9R)-9-azidomethyl-16-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-14-methoxy-13-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecin-6,12-dione as a foam

Workup

customevaporated in vacuo
customThe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-fab462d7e7a4408fabea24769702f09e
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665746

Reaction notes

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