3(R)-ethyl-5(S)-[5-benzyloxy-1(S)-tert-butoxy-carbonylamino-3,3-dimethyl-pentyl]-2-oxo-tetrahydrofuran → 3-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-ethyl-propionic acid (N-butyl)amide

HRID 863321Notes

Reaction equation

HRID 863321 reaction equation
C([C@@H]1C[C@@H]([C@@](N=C=O)(OC(C)(C)C)CC(C)(C)CCOCC2C=CC=CC=2)[O:5]C1=O)C.C(NC(=O)[C@H](C)C[C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC(C)(C)CC(N1C2C(=CC=CC=2)CC(COCC=C)C1)=O)CCC.[CH2:75]([NH:79][C:80](=[O:113])[C@H:81]([CH2:111][CH3:112])[CH2:82][C@@H:83]1[O:87][C:86]([CH3:89])([CH3:88])[N:85]([C:90]([O:92][C:93]([CH3:96])([CH3:95])[CH3:94])=[O:91])[C@H:84]1[CH2:97][C:98]([CH3:110])([CH3:109])[CH2:99][CH2:100][O:101]CC1C=CC=CC=1)[CH2:76][CH2:77][CH3:78].C(NC(=O)[C@H](C)C[C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC(C)(C)CC(N1C2C(=CC=CC=2)CC(NC(C2CC2)=O)C1)=O)CCC>>[CH2:75]([NH:79][C:80](=[O:113])[C@H:81]([CH2:111][CH3:112])[CH2:82][C@@H:83]1[O:87][C:86]([CH3:89])([CH3:88])[N:85]([C:90]([O:92][C:93]([CH3:94])([CH3:95])[CH3:96])=[O:91])[C@H:84]1[CH2:97][C:98]([CH3:109])([CH3:110])[CH2:99][C:100]([OH:101])=[O:5])[CH2:76][CH2:77][CH3:78]

Participants

5

Reactant 4

HCID 867521113(R)-ethyl-5(S)-[5-benzyloxy-1(S)-tert-butoxy-carbonylamino-3,3-dimethyl-pentyl]-2-oxo-tetrahydrofuranHCID 867521123-[N-tert-butoxycarbonyl-4(S)-(4-benzyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-ethyl-propionic acid (N-butyl)amideHCID 1317205275(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-cyclopropylcarbonylamino-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amideHCID 1317205295(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-allyloxymethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide2×

Product 1

HCID 867521103-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-ethyl-propionic acid (N-butyl)amide

Procedure

Starting from 200 mg of 3(R)-ethyl-5(S)-[5-benzyloxy-1(S)-tert-butoxy- carbonylamino-3,3-dimethyl-pentyl]-2-oxo-tetrahydrofuran via 2(R)-ethyl-9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-butyl)amide (Rf (A)=0.28; FAB-MS: (M+H)+ =507), 3-[N-tert-butoxycarbonyl-4(S)-(4-benzyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-ethyl-propionic acid (N-butyl)amide (Rf (B)=0.46; FAB-MS: (M+H)+ =547) and 3-[N-tert-butoxycarbonyl-4(S)-(2,2-dimethyl-4-hydroxybutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-ethyl-propionic acid (N-butyl)amide (Rf (A)=0.24; FAB-MS: MS:(M+H)+ =457) in a manner analogous to that described in Examples 74a,74b and 74c), as the pure diastereomer: Rf (P)=0.58; FAB-MS:(M+H)+ =471.

Sources & evidence

ORD record
ord-51ae9722633b4a639d57707094a16885
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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