2(R)-but-2-enyl-9-tert-butyldiphenylsilyloxy-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-butyl)amide → 3-[N-tert-butoxycarbonyl-4(S)-(4-tert-butyl-diphenylsilyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide

HRID 863331Notes

Reaction equation

[CH2:1]([C@@H:5]1C[C@@H]([C@@H](NC(OC(C)(C)C)=O)CC(C)(C)CCO[Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)OC1=O)[CH:2]=CC.[CH2:44]([NH:48][C:49](=[O:91])[C@H:50]([CH2:87][CH:88]=[CH:89][CH3:90])[CH2:51][C@H:52]([OH:86])[C@@H:53]([NH:78][C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[CH2:54][C:55]([CH3:77])([CH3:76])[CH2:56][CH2:57][O:58][Si:59]([C:72]([CH3:75])([CH3:74])[CH3:73])([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[CH2:45][CH2:46][CH3:47].C(NC(=O)[C@H](CC(C)=C)C[C@@H]1OC(C)(C=C=O)N(OC(C)(C)C)[C@H]1CC(C)(C)CCOCC1C=CC=CC=1)CCC>>[CH2:44]([NH:48][C:49](=[O:91])[C@H:50]([CH2:87][CH:88]=[CH:89][CH3:90])[CH2:51][C@@H:52]1[O:86][C:1]([CH3:5])([CH3:2])[N:78]([C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80])[C@H:53]1[CH2:54][C:55]([CH3:76])([CH3:77])[CH2:56][CH2:57][O:58][Si:59]([C:72]([CH3:74])([CH3:73])[CH3:75])([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)[CH2:45][CH2:46][CH3:47]

Participants

Reactant 3

HCID 572611992(R)-but-2-enyl-9-tert-butyldiphenylsilyloxy-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-butyl)amide

HCID 676259163(R)-But-2-enyl-5(S)-[5-tert-butyl-diphenylsilyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxo-tetrahydrofuran

HCID 867521153-[N-tert-butoxy-carbonyl-4(S)-(4-benzyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-[(2-methyl)propen-3-yl]-propionic acid (N-butyl)amide

Product 1

HCID 1317205373-[N-tert-butoxycarbonyl-4(S)-(4-tert-butyl-diphenylsilyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide

Procedure

Starting from 472 mg of 3(R)-but-2-enyl-5(S)-[5-tert-butyl-diphenylsilyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxo-tetrahydrofuran via 2(R)-but-2-enyl-9-tert-butyldiphenylsilyloxy-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-butyl)amide (Rf (A)=0.64; FAB-MS: (M+H)+ =681) analogously to Examples 74b and 74c): Rf (B)=0.71; FAB-MS: (M+H)+ =721.

Sources & evidence

ORD record: ord-73884d7e134f4e6fb52a6f6683734351
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719141

Reaction notes

Loading…