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

HRID 863327Notes

Reaction equation

HRID 863327 reaction equation
[CH2:1]([NH:5][C:6](=[O:32])[C@H:7]([CH3:31])[CH2:8][C@@H:9]1[O:13]C(C)(C)[N:11](C(OC(C)(C)C)=O)[C@H:10]1[CH2:23][C:24]([CH3:30])([CH3:29])[CH2:25][C:26]([OH:28])=O)[CH2:2][CH2:3][CH3:4].[C:33]([CH2:36][CH2:37][CH:38]1[CH2:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[NH:40][CH2:39]1)(=[O:35])[NH2:34]>>[CH2:1]([NH:5][C:6](=[O:32])[C@H:7]([CH3:31])[CH2:8][C@H:9]([OH:13])[C@@H:10]([NH2:11])[CH2:23][C:24]([CH3:29])([CH3:30])[CH2:25][C:26]([N:40]1[C:41]2[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:47][CH:38]([CH2:37][CH2:36][C:33](=[O:35])[NH2:34])[CH2:39]1)=[O:28])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 196977953(R,S)-(2-carbamoyl)ethyl-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)amide

Product 1

HCID 1317205365(S)-Amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-(2-carbamoyl)ethyl-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 205 mg of 3(R,S)-(2-carbamoyl)ethyl-1,2,3,4-tetrahydroquinoline, the title compound is obtained via (4O,5N-isopropylidene)-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-(2-carbamoyl)ethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide (analogously to Example 1a); Rf (X)=0.08; Rf (V)=0.56; Rt (VI)=30.8 min) and 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-(2-carbamoyl)ethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide (Rf (P)=0.32; Rt (VI)=26.8 min; FAB-MS: (M+H)+ =603) in a manner analogous to Example 1) as a diastereomer mixture: Rf (V)=0.21; Rt (VI)=20.3 min; FAB-MS: (M+H)+ =503.

Sources & evidence

ORD record
ord-460250453a5a4e958e1022f92a359c98
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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