3(R,S)-methoxyethyl-1,2,3,4-tetrahydroquinoline → 5(S)-Amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxyethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

HRID 863318Notes

Reaction equation

HRID 863318 reaction equation
C(NC(=O)[C@H](C)C[C@@H]1OC(C)(C)N(C(OC(C)(C)C)=O)[C@H]1CC(C)(C)CC(O)=O)CCC.COCCC1CC2C(=CC=CC=2)NC1.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.[CH2:90]([NH:94][C:95](=[O:131])[C@H:96]([CH3:130])[CH2:97][C@H:98]([OH:129])[C@@H:99]([NH:121]C(OC(C)(C)C)=O)[CH2:100][C:101]([CH3:120])([CH3:119])[CH2:102][C:103]([N:105]1[C:114]2[C:109](=[CH:110][CH:111]=[CH:112][CH:113]=2)[CH2:108][CH:107]([CH2:115][CH2:116][O:117][CH3:118])[CH2:106]1)=[O:104])[CH2:91][CH2:92][CH3:93].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=2OC(C=NOC)C1)=O)CCC>>[CH2:90]([NH:94][C:95](=[O:131])[C@H:96]([CH3:130])[CH2:97][C@H:98]([OH:129])[C@@H:99]([NH2:121])[CH2:100][C:101]([CH3:119])([CH3:120])[CH2:102][C:103]([N:105]1[C:114]2[C:109](=[CH:110][CH:111]=[CH:112][CH:113]=2)[CH2:108][CH:107]([CH2:115][CH2:116][O:117][CH3:118])[CH2:106]1)=[O:104])[CH2:91][CH2:92][CH3:93]

Participants

6

Reactant 5

HCID 196978553(R,S)-methoxyethyl-1,2,3,4-tetrahydroquinolineHCID 867520953-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic 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)amideHCID 1317205315(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[2(R,S)-methoxyiminomethyl-3,4-dihydro-2H-1,4-benzoxazin-4-ylcarbonyl]-octanoic acid (N-butyl)amideHCID 1317205335(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxyethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

Product 1

HCID 1317205325(S)-Amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxyethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

Procedure

Starting from 230 mg of 3-[N-tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide and 287 mg of 3(R,S)-methoxyethyl-1,2,3,4-tetrahydroquinoline via (4O,5N-isopropylidene)-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxyethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide (analogously to Example 1a); Rf (A)=0.17; Rt (VI)=35.8 min) and 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methoxyethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide (Rf (V)=0.81; Rt (VI)=31.0 min) in a manner analogous to that described in Example 1) as a diastereomer mixture: Rf (V)=0.44; Rt (VI)=23.6 min; FAB-MS: (M+H)+ =490.

Sources & evidence

ORD record
ord-55865f3438534a458126f410e407a7c9
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

Loading…