HCID 59997285, compound → HCID 86635526, compound

HRID 1253997Notes

Reaction equation

[C:1](C1C=C(C=CC=1)COC1C=CC(C[C@]2(S(C3C=CC4OCOC=4C=3)(=O)=O)[C@@H](CC(C)C)OC(C)(C)N2CN)=CC=1)#[N:2].[CH2:43]([O:50][C:51]1[CH:89]=[CH:88][C:54]([CH2:55][C@H:56]([NH:76][C:77](=[O:87])[O:78][C@@H:79]2[C@H:86]3[C@H:82]([O:83][CH2:84][CH2:85]3)[O:81][CH2:80]2)[C@H:57]([OH:75])[CH2:58][N:59]([S:64]([C:67]2[CH:72]=[CH:71][C:70]([OH:73])=[C:69]([CH3:74])[CH:68]=2)(=[O:66])=[O:65])[CH2:60][CH:61]([CH3:63])[CH3:62])=[CH:53][CH:52]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[C:1]([C:48]1[CH:49]=[C:44]([CH:45]=[CH:46][CH:47]=1)[CH2:43][O:50][C:51]1[CH:52]=[CH:53][C:54]([CH2:55][C@H:56]([NH:76][C:77](=[O:87])[O:78][CH:79]2[CH:86]3[CH:82]([O:83][CH2:84][CH2:85]3)[O:81][CH2:80]2)[C@H:57]([OH:75])[CH2:58][N:59]([S:64]([C:67]2[CH:72]=[CH:71][C:70]([OH:73])=[C:69]([CH3:74])[CH:68]=2)(=[O:65])=[O:66])[CH2:60][CH:61]([CH3:62])[CH3:63])=[CH:88][CH:89]=1)#[N:2]

Participants

Reactant 2

HCID 59997285HCID 59997285, compound

HCID 69012050HCID 69012050, compound

Product 1

HCID 86635526HCID 86635526, compound

Procedure

The alkylation step was carried out as described for N-(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl-oxycarbonyl-, (4S,5R)-4-[4-(3-cyanobenzyloxy)-benzyl]-5-i-butyl-[(3,4-methylenedioxyphenyl)sulfonyl]-aminomethyl-2,2-dimethyl-oxazolidine. The deacetylation step was carried out as described previously for (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[[(4-hydroxy-3-methylphenyl)sulfonyl](isobutyl)amino]propylcarbamate. The final product was isolated by preparative HPLC. (Column: Luna C18, Solvent: 75% to 100% MeOH/0.1% formic acid, tret: 4.08 min.) (Y=6%, 2 steps, overall.)

Sources & evidence

ORD record: ord-3ec2c78691a64b3e9920f1fed3971fc1
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455497B2

Reaction notes

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